Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry Supporting Information
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- Ἄμμων Λύκος
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1 Supporting Information Unexpected Nucleophilic Behaviour of Radicals Generated from α-iodoketones Corinne De Dobbeleer, a Ji í Pospíšil, a Freija De Vleeschouwer, b Frank De Proft b and István E. Markó a, * a Université catholique de Louvain, Département de Chimie, Bâtiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium b Eenheid Algemene Chemie (ALGC), Vrije Universiteit Brussel (VUB), Faculteit Wetenschappen, Pleinlaan 2, 1050 Brussels, Belgium marko@chim.ucl.ac.be Table of contents Full notation of reference General information...3 Table S-1: The reaction of α-iodoketone 4c with electron rich olefins....4 Table S-2: The addition of 4c to 5a. The reaction optimization (part I)...5 Table S-2: The addition of 4c to 5c. The reaction optimization (part II)...6 Table S-3: Activation barriers (DE π at 0K and DH π at K) and reaction energies (DE R at 0K and DE R at K) for the addition of the three different radicals to substituted alkenes R- CH=CH 2. All values are in kcal/mol and were obtained at the B3LYP/6-31+G(d) //B3LYP/6-31+G(d) level of theory using the Gaussian03 program...7 Synthesis of unknown α-iodoketones...8 General procedure for radical coupling reaction...13 I. Structural data for Table 3 : B3LYP/6-311+G(d,p) geometries...21 (Cartesian coordinates, all values in Å)...21 II. Structural data for Table S-3 : B3LYP/6-31+G(d) geometries...24 (Cartesian coordinates, all values in Å) H and 13 C-NMR spectras...48 S-1
2 Full notation of reference 14 Gaussian 03, Revision D.01, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao,.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev,.; Austin, A. J.; Cammi, R.; Pomelli, C.; chterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas,.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; rtiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al- Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A.; Gaussian, Inc., Wallingford CT, S-2
3 General information All compounds (Acros, Aldrich and Fluka) were used as received. THF was distilled under argon from sodium benzophenone ketyl. Flash chromatography was performed on silica gel 60 (40-63 μm) (RCC). 1 H and 13 C-NMR spectra were recorded on a Varian Gemini-2000 (working frequency 300 MHz and 75 MHz, respectively), on a Bruker AC-250 (working frequency 250 MHz and 62.5 MHz, respectively), on a Brucker AC-300 Avance II (working frequency 300 MHz and 75 MHz, respectively) or on a Brucker AM-500 (working frequency 500 MHz and 125 MHz, respectively) at ambient temperature in CDCl 3 (Aldrich). Mass spectra were recorded on a Finigan TSQ All reactions were carried out under an atmosphere of argon in flame-dried apparatus with magnetic stirring, unless otherwise indicated. The identity of known products was confirmed by comparison with literature spectroscopic data. The structure determination of new compounds was made with a help of 2D-CSY, HSQC, HMBC, 2D-NESY and NEdiff experiments: 4a,b, 1 4d, 2 4e, 3 4k, 4 8, 5 and 9 6. The α-iodoketones 4a-d,h,i,l 1 and 4f 3 were prepared according to published procedures. S-3
4 Table S-1: The reaction of α-iodoketone 4c with electron rich olefins. I H H I X Bu c S-1 S-2 S-3 S-4 Entry Conditions 1 b nbu 3 SnH (1.0 equiv), AIBN (0.2 equiv), benzene, Δ, 2h nbu 2 3 Snallyl (1.5 equiv), AIBN (0.2 equiv), benzene, Δ, 12h Product(s), (Yield(%)) a 4c (<5%), S-1 (quant) 4c (~50%), S-1 (<5%), S-2 (<5%) 3 nbu 3 Snallyl (1.5 equiv), hν, benzene, r.t., 48h degradation 4 c Sn(allyl) 4 (2.0 equiv), AIBN (0.2 equiv), toluene, Δ, 24h allylmgcl (3.0 equiv), GaCl 3 (3.0 equiv), Et 3 B(0.5equiv),H 2 /THF, r.t, 2h allylmgcl (3.0 equiv), Cp 2 ZrCl 2 (3.0 equiv), Et 3 B (0.5 equiv), THF, r.t, 2h allylsime 3 (2.0 equiv), Yb(Tf) 3 (1.0 equiv), Et 3 B (0.5 equiv), THF, r.t, 2h allylh (5.0 equiv), Et 3 B(1.0equiv), bezene, r.t, 2h allylh (5.0 equiv), Et 3 B(1.0equiv),EtH, r.t, 2h CH 2 =CHBu (10.0 equiv), AIBN (0.2 equiv), toluene, Δ, 3h CH 2 =CHBu (10.0 equiv), hν, K 2 C 3 (10.0 equiv), MeH, r.t., 3h nbu 3 SnH (1.0 equiv), AIBN (0.2 equiv), toluene/ch 2 =CHBn = 1:1, 90 C, 3h 4c (41%), S-1 (<5%), S-2 (19%) 4c (<5%), S-1 (91%), S-2 (<5%) 4c (<5%), S-1 (60%), S-2 (<5%) 4c (<5%), S-1 (95%), S-2 (<5%) 4c (<5%), S-1 (45%), S-3 (<5%) 4c (<5%), S-1 (80%), S-3 (<5%) degradation degradation degradation a Refers to pure, isolated compounds. b Reference reaction. To prove that the radical is formed. c The reaction proved to be irreproducible. The best obtained result shown. S-4
5 Table S-2: The addition of 4c to 5a. The reaction optimization (part I). 4c I + Br C 2 Et 5a AIBN (0.2 equiv) benzene, 80 C 6c C 2 Et Entry 5a (equiv) Bu 6 Sn 2 (equiv) Yield(%) a a Refers to pure, isolated compounds. S-5
6 Table S-2: The addition of 4c to 5c. The reaction optimization (part II). 4c I + S 2 Et C 2 Et 5c AIBN (0.2 equiv) benzene, 80 C 6c C 2 Et Entry 5c (equiv) Time (h) Product(s) (Yield(%)) a c (62%), 6c (12%) c (51%), 6c (19%) c (48%), 6c (23%) c (10%), 6c (62%) c (<5%), 6c (82%) c (<5%), 6c (89%) a Refers to pure, isolated compounds. S-6
7 Table S-3: Activation barriers (DE π at 0K and DH π at K) and reaction energies (DE R at 0K and DE R at K) for the addition of the three different radicals to substituted alkenes R-CH=CH 2. All values are in kcal/mol and were obtained at the B3LYP 7 /6-31+G(d) 8 //B3LYP/6-31+G(d) level of theory using the Gaussian03 program. 9 Radical R=CH 3 R=CH 3 R=CCH 3 DE π DH π DE R DE R DE π DH π DE R DE R DE π DH π DE R DE R S-7
8 Synthesis of unknown α-iodoketones Synthesis of α-iodoketone 4c TMSCl, NaI Et 3 N, CH 3 CN SiMe S-5 S-6 11 NIS CH 2 Cl I c A solution of sodium iodide (3.6 g, mol, 1.25 equiv) in acetonitrile (30 ml) was added to neat cyclodecanone S-5 (3.0 g, mol, 1.0 equiv), chloro(trimethyl)silane (2.6 g, mol, 1.25 equiv) and triethylamine (2.5 g, mol, 1.25 equiv). The reaction mixture was stirred at rt under inert atmosphere for 17h. The organic layer was extracted with pentane (3x20 ml). The pentane layer was dried over MgS 4 and evaporated under reduced pressure to give the desired product S-6 10 as colorless liquid (4.25 g, Z: E 2:1, 99%). 1 H-NMR (300 MHz, CDCl 3 ) δ(ppm): 0.10 and 0.13 (2 s, 9H, H-11), (m, 12H, H-4 to 8), 1.93 (t, 2H, J= 6 Hz, H-2), and (2 m, 2H, H-9), 4.49 (t, J= 8.4 Hz, H-10 E) and 4.57 (t, J= 7.6 Hz, H-10 Z) (1H). 13 C-NMR (50 MHz, CDCl 3 ) δ(ppm): 0.5 (C-11), 21.0 (C-3), (C-4), 24.9 (C-5), 25.6 (C-6), 26.4 (C-7), 26.7 (C-8), 27.4 (C-9 Z), 28.2 (C-9 E), 29.0 (C-2 E), 37.6 (C-2 Z), (C-10 E), (C-10 Z), (C-1 Z), (C-1 E). A solution of S-6 (4.2 g, 18 mmol, 1.0 equiv) in CH 2 Cl 2 (70 ml) was cooled to 0 C and N- iodosuccinimide (4.1 g, 18 mmol, 1.0 equiv) was added. The reaction mixture was kept at this temperature for 30 min. The reaction mixture was diluted with CH 2 Cl 2 (50 ml) and washed with a saturated aqueous solution of Na 2 S 2 3 (2x50 ml) and water (1 x 50 ml), dried over MgS 4 and the solvent was removed under reduced pressure. After purification by flash column chromatography (PE : EtAc, 98:2, Rf=0.3), the desired product 4c was obtained in 89 % yield (4.5 g) as a slightly yellow oil. 1 H-NMR (300 MHz, CDCl 3 ) δ(ppm): (m, 13H, one of H-3 and H-4 to 9), (m, 2H, one of H-2 and one of H-3), (m, 1H, one of H-2), 4.90 (dd, J= 3.9Hz, J= 12Hz, 1H, H-10). 13 C- NMR (75 MHz, CDCl 3 ) δ(ppm): 23.6, 24.0, 24.6, 25.3, 25.4, 25.5, 29.2, 35.7, 37.0 (C-2 to C-10), (C-1). S-8
9 Synthesis of α-iodoketone 4e 1) HN(TMS) 2,TMSI CH 2 Cl 2 S-7 2) NaI, mcpba THF I 4e A solution of S-7 (290 μl, 2.5 mmol, 1.0 equiv) in CH 2 Cl 2 (13 ml) was cooled to 0 C and HN(TMS) 2 (1.04 ml, 5.0 mmol, 2.0 equiv) was added dropwise. After 5 minutes, TMSI (427 μl, 3.0 mmol, 1.2 equiv) was added dropwise. The resulting mixture was stirred at 0 C for 20 minutes and then for an additional 20 minutes at rt. The reaction mixture was again cooled to 0 C before the slow addition of a cold (0 C) solution of NaI (411 mg, 2.75 mmol, 1.1 equiv) and mcpba (475 mg, 2.75 mmol, 1.1 equiv) in THF (16 ml). This solution was prepared by portion-wise addition of NaI to a cold (0 C) solution of mcpba in THF. After 1.5h at 0 C, the mixture was diluted with Et 2 /H 2 = 2:1 (90 ml) and the resulting layers were separated. The aqueous layer was extracted with Et 2 (3x30 ml). The combined organic layers were washed with a saturated aqueous solution of Na 2 S 2 3 (30 ml), brine (30 ml), dried over Na 2 S 4 and the solvents were removed under reduced pressure. After purification by flash column chromatography (PE:Et 2 = 10:1), the desired α-iodoketone 4e (493 mg, 88%)was obtained as a slightly yellow oil. 1 H-NMR (300 MHz, CDCl 3 ) δ(ppm): 2.42 (s, 3H, H-1), 2.68 (ddd, 1H, J = 14.7, 7.4 and 1.1 Hz, one of H- 4), 2.80 (ddd,1h, J = 14.7, 6.8, 1.0 Hz, one of H-4), 4.51 (t, 1H, J = 7.5 Hz, H-3), (m, 2H, H-6), (m, 1H, H-5); 13 C-NMR (75 MHz, CDCl 3 ) δ(ppm): 26.4, 31.2, 38.9, 118.6, 135.2, Synthesis of α-iodoketone 4i ) HN(TMS) 2,TMSI I CH 2 Cl 2 S-8 2) NaI, mcpba THF Prepared according to the same protocol as α-iodoketone 4e. After purification by flash column chromatography (P.E.:Et 2 = 20:1), the desired α-iodoketone 4i (614 mg, 93%) was obtained as a slightly yellow oil. 1 H-NMR (300 MHz, CDCl 3 ) δ(ppm): (m, 6H, H-3 to H-5), 2.22 (ddd, 1H, J = 15.6, 6.0, 3.0 Hz, one of H-6), 2.39 (ddd, 1H, J = 15.2, 4.2, 2.2 Hz, one of H-6), 2.73 (dd,1h, J = 14.8, 7.0 Hz, one of H-7), 3.05 (dd, 1H, J = 14.8, 7.0 Hz, one of H-7), (m, 2H, H-9), (m, 1H, H-8); 13 C-NMR (100 MHz, CDCl 3 ) δ(ppm): 23.7, 26.6, 36.5, 41.9, 46.5, 56.4 (C-2), (C-9), (C-8), 205.1(C-1) i 9 S-9
10 Synthesis of α-iodoketone 4k + S-9 S-10 I 1) HNTMS 2,TMSI 1 CH 2 Cl 2 2 2) NaI, mcpba THF 6 7 Prepared according to the same protocol as α-iodoketone 4e. After purification by flash column chromatography (PE:Et 2 = 30:1), the desired α-iodoketone 4k (736 mg, 92%) was obtained as a slightly yellow oil. 1 H-NMR (500 MHz, CDCl 3 ) δ(ppm): 0.94 (s, 9H, H-11), (m, 1H, H-4), (m, 1H), 1.65 (dt, J = 13.5, 6.2 Hz, 1H), (m, 1H), 2.23 (dt, J = 15.4, 3.2 Hz, 1H, one of H-3), 2.43 (ddd, J = 15.4, 4.2, 2.6 Hz, 1H, one of H-3), 2.76 (dd, J = 14.8, 7.0 Hz, 1H, one of H-7), 3.07 (dd, J = 14.8, 7.1 Hz, 1H, one of H-7), (m, 1H), (m, 2H, H-9), 5.87 (ddt, J = 17.2, 10.2, 7.0 Hz, 1H, H-8) 13 C-NMR (100 MHz, CDCl 3 ) δ(ppm): 27.8 (C-11), 28.1, 34.3 (C-10), 36.4, 43.1, 45.1, 47.0, 61.7 (C-2), (C-9), (C-8), (C-1) k 9 H H H H H H I observed NE effect Synthesis of α-iodoketone 4g H Hg yellow,i CCl 4 7 I S-11 4g Hg yellow (210 mg, 0.97 mmol, 3 equiv) and iodine (240 mg, 0.95 mmol, 2.9 equiv) were added to a solution of (3aS*,7aR*)-7a-hydroxyperhydro-4-indenone S (50 mg, 0.32 mmol, 1 equiv) in CCl 4 (5 ml). The reaction mixture was stirred at rt under irradiation (visible light) for 3 hours. The solution was filtrated over Celite and the filter cake was washed with CH 2 Cl 2 (3 x 3 ml). The resulting solution was treated with a saturated aqueous solution of Na 2 S 2 3 (2 x 10 ml) and water (2 x 10 ml). The organic layer was separated, dried over MgS 4 and the solvents were removed under reduced pressure. 6-Iodocyclononane-1,5-dione 4g (85 mg, 93 %) was obtained as a yellow solid (mp = C). 5 4 S-10
11 IR (film): 2954 cm -1 (stretching C-H), 1700 (C=), 1462, 1442, 1359, 1316, 1100, 732 cm H-NMR (500 MHz, CDCl 3 ) δ(ppm): (m, 1H, one of H-8), (m, 1H, one of H-8), (m, 3H, H-3 and one of H-7), (m, 4H, one of H-4, H-9, one of H-7), 2.49 (ddd, J = 10.8 Hz, J = 6.0 Hz, J = 3.6Hz, 1H, one of H-4), (m, 2H, H-2), 4.37 (dd, J = 12.3 Hz, J = 3.7 Hz, 1H, H-6). 13 C- NMR (125 MHz, CDCl 3 ) δ(ppm): 21.36, 24.46, (C-6), 33.95, 34.20, 38.78, 41.60, (C-5), (C-1). MS (EI, 70 ev) m/z (relative intensity): (M + ) 280 (12 %); (M + -I) 153 (77%); ( H2) 135 (92 %); ( C 2 H 4 ) 125 (43 %); 107 (90%); 97 (61%); 84 (42%); 55 (100%). Synthesis of α-iodoketone 4h H Hg yellow,i 2 CCl S-12 4h I Hg yellow (75 mg, 0.34 mmol, 3 equiv) and iodine (85 mg, 0.33 mmol, 2.9 equiv) were added to a solution of 4a-hydroxyperhydrobenzo[a]cyclohepten-1-one S (21 mg, 0.11 mmol, 1 equiv) in CCl 4 (1.5 ml). The reaction mixture was stirred at rt under irradiation (visible light) for five hours. The solution was filtrated over Celite and the filter cake was washed with CH 2 Cl 2 (3 x 4 ml). The resulting solution was treated with a saturated aqueous solution of Na 2 S 2 3 (2 x 10mL) and water (2 x 10mL). The organic layer was separated, dried over MgS 4 and the solvents were removed under reduced pressure. 6-iodocycloundecane-1,5-dione 4h (31 mg, 90%) were obtained as a yellow solid (mp = C). IR (film): 2938, 2875 and 2848 cm -1 (stretching C-H), 1703 (C=), 1460, 1436, 1367, 1189, 1087 cm H-NMR (200 MHz, CDCl 3 ) δ(ppm): (m, 4H), (m, 8H), (m, 2H), 2.77 (ddd, J = 17.3, 6.6, 4.9 Hz, 1H, one of H-2), 2.95 (ddd, J = 17.4, 8.2, 5.1 Hz, 1H, one of H-2), 4.28 (dd, J = Hz, 1H, H-6). 13 C-NMR (50 MHz, CDCl 3 ) δ(ppm): 18.30, 22.97, 26.18, 26.88, (C-6), 33.84, 34.30, 40.17, 41.63, (C-5), (C-1). MS (EI, 70 ev) m/z (relative intensity): (M + ) 308 (6 %); (M + -H. ) 307 (6 %); (M + -H 2 ) 306 (20 %); (M + -I) 181 (100 %); ( H 2 ) 163 (40 %); 97 (35%); 55 (80%). S-11
12 Synthesis of α-iodoketone 4l H Hg yellow,i 2 CCl S-12 4l 1 6 I Hg yellow (268 mg, 1.23 mmol, 3 equiv) and iodine (304 mg, 1.19 mmol, 2.9 equiv) were added to a solution of 4a-hydroxy-5-methyloctahydro-1(2H)-naphtone S (75 mg, 0.41 mmol, 1 equiv) in CCl 4 (1.5 ml). The reaction mixture was stirred at rt under irradiation (visible light) for 5 hours. The solution was filtrated over celite and the filter cake was washed with CH 2 Cl 2 (3 x 5 ml). The resulting solution was treated with a saturated aqueous solution of Na 2 S 2 3 (2 x 10 ml) and water (2 x 10 ml). The organic layer was separated, dried over MgS 4 and the solvents were removed under reduced pressure. cis-6-iodo-10-methylcyclodecane-1,5-dione 4l (119 mg, 94%) was obtained as a yellow solid (mp = C). IR (film): 3008, 2969, 2940 and 2887 cm -1 (stretching C-H), 1702 (C=), 1466, 1375, 1194, 1083, 905, 740 cm H-NMR (500 MHz, CDCl 3 ) δ(ppm): 1.00 (d, J= 6.7 Hz, 3H, H-11), (m, 1H, one of H-8), (m, 1H, one of H-9), (m, 2H, one of H-8 and one of H-9), (m, 1H, one of H-3), (m, 3H, one o f H-3 and H-7), 2.39 (ddd, J = 17.6, 5.6 Hz, J = 4.0 Hz, 1H, one of H-4), (m, 3H, one of H-2, one of H-4 and H-10), 2.98 (ddd, J = 15.0, 10.2 Hz, J = 4.0 Hz, 1H, one of H-2), 4.31 (dd, J =11.7, 4.0 Hz, 1H, H-6). 13 C-NMR (125 MHz, CDCl 3 ) δ(ppm): (C-11), (C- 3), (C-8), (C-9), (C-6), (C-2), (C-7), (C-4), (C-10), (C- 5), (C-1). MS (EI, 70 ev) m/z (relative intensity): (M + ) 308 (46 %), (M + -I) 181 (93 %), 139 (45%), 111 (50%), 97 (52%), 55 (95%), 42 (100%). S-12
13 General procedure for radical coupling reaction Method A: A solution of α-iodoketone 4 (0.2 mmol, 1.0 equiv), ethyl 2-(bromomethyl)acrylate 5a (116 mg, 80 μl, 0.6 mmol, 3.0 equiv), nbu 6 Sn 2 (139 mg, 120 μl, 0.24 mmol, 1.2 equiv) and AIBN (7 mg, 0.04 mmol, 0.2 equiv) in benzene (1 ml) refluxed for 2.5h. The resulting solution was evaporated under reduced pressure and the residue was purified by flash column chromatography. Method B: A solution of α-iodoketone 4a (42 mg, 0.2 mmol, 1.0 equiv), ethyl 2- (tributyltinmethyl)acrylate 5b (121 mg, 0.3 mmol, 1.5 equiv), and AIBN (7 mg, 0.04 mmol, 0.2 equiv) in benzene (1 ml) refluxed for 4h. The resulting solution was evaporated under reduced pressure and the residue was purified by flash column chromatography. Method C: A solution of α-iodoketone 4 (0.2 mmol, 1.0 equiv), ethyl 2-(ethylsulfonemethyl)acrylate 5c (413 mg, 0.3 mmol, 10.0 equiv), and AIBN (7 mg, 0.04 mmol, 0.2 equiv) in benzene (1 ml) refluxed for 2h. The resulting solution was evaporated under reduced pressure and the residue was purified by flash column chromatography. Adduct 6a 12 Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 9:1 4:1) to give 35.3 mg (90%) of 6a. Method B: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 9:1 4:1, Rf = 0.25) to give 36.1 mg (92%) of 6a. S-13
14 Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fractions; P.E : Et 2 = 5:1 CH 2 Cl 2 :MeH = 100:1 ) to give 37.7 mg (96%) of 6a and 224 mg (5.4 equiv.) of 5c H-NMR (500 MHz, CDCl 3 ) δ(ppm): 1.30 (t, J = 7.1 Hz, 3H, H-1), (m, 1H), (m, 1H), (m, 1H), (m, 3H), (m, 2H), 2.83 (ddd, J = 14.0, 4.2, 0.8 Hz, 1H, one of H- 6), 4.21 (q, J = 7.1 Hz, 2H, H-2), 5.57 (s, 1H, one of H-5), 6.20 (s, 1H, one of H-5); 13 C-NMR (125 MHz, CDCl 3 ) δ(ppm): 14.1 (C-1), 20.4, 29.3, 32.0, 37.8 (C-10), 48.3 (C-7), 60.7 (C-2), (C-5), (C-4), (C-3), (C-11); MS (CI, CH 4 -N 2 ) m/z (relative intensity): [M+H] (57 %); 151 (100%); 133 (12%); 123 (37%); 105 (24%); 95 (56%); 93 (9%); 79 (34%); 67 (36%); 55 (9%); 43 (9 %). CAS : Adduct 6b 12 Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 9:1 4:1) to give 35.6 mg (85%) of 6b. Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 5:1 CH 2 Cl 2 :MeH = 100:1 ) to give 38.7 mg (92%) of 6b and 202 mg (4.9 equiv.) of 5c H-NMR (300 MHz, CDCl 3 ) δ(ppm): 1.25 (t, J = 7.1 Hz, 3H, H-1), (partial overlap, m, 1H), (m, 2H), (m, 1H), (m, 3H), (m, 2H), (m, 1H), 2.87 (dd, J = 13.8, 4.8 Hz, 1H, one of H-6), 4.15 (q, J = 7.2 Hz, 2H, H-2), 5.52 (d, J = 1.5 Hz, 1H, one of H-5), 6.15 (d, J = 1.5 Hz, 1H, one of H-5); 13 C-NMR (62.5 MHz, CDCl 3 ) δ(ppm): 14.2 (C-1), 25.1, 28.1, 32.0, 33.6, 42.1 (C-11), 49.2 (C-7), 60.6 (C-2), (C-5), (C-4), (C-3), (C-11); MS (CI, CH 4 - N 2 ) m/z (relative intensity): [M+H] (52 %); [M] (8%); 193 (6 %); 182 (8 %); 166 (10 %); 165 (100 %); 164 (9 %); 136 (9 %). S-14
15 Adduct 6c Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 50:1 9:1) to give 37.3 mg (70%) of 6c as a colorless oil. Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 10:1 CH 2 Cl 2 :MeH = 100:1 ) to give 47.5 mg (89%) of 6c and 241 mg (5.8 equiv) of 5c IR: 2927, 2871, 1629, 1472, 1445, 1369, 1326, 1179, 1137, 1026, 950, 819, 737 cm -1 1 H-NMR (300 MHz, CDCl 3 ) δ(ppm): 1.28 (t, J = 7.2 Hz, 3H, H-1), (m, 16H), (m, 2H), 2.61 (ddd, J = 16.2, 9.0, 3.3 Hz, 1H), (m, 1H), 4.18 (q, J = 7.2 Hz, 2H, H-2), 5.48 (s, 1H, one of H-5), 6.12 (d, J = 1.5 Hz, 1H, one of H-5); 13 C-NMR (75 MHz, CDCl 3 ) δ(ppm): 14.1 (C-1), 23.0, 23.3, 23.5, , 24.8, 25.1, 25.2, 42.3 (C-15), 50.3 (C-7), 60.7 (C-2), (C-5), (C-4), (C-3), (C-16)]; MS (CI, CH 4 -N 2 ) m/z (relative intensity): [M+H] (100 %), 249 (23 %), 181 (17 %), 174 (13 %), 162 (8 %); HRMS (CI + ): calculated mass for C 16 H 27 3 ( , [M+H] + ), found ( ). Adduct 6d Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 50:1) to give 41.8 mg (71%) of 6d as a colorless oil. Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 20:1 CH 2 Cl 2 :MeH = 100:1 ) to give 51.9 mg (88%) of 6d and 215 mg (5.2 equiv) of 5c IR: 2932 and 2864 cm -1 (stretching C-H), 1718 cm -1 (C=), 1628 cm -1 (C=C-C=), 1469, 1411, 1368, 1326, 1188, 1140, 1025, 946 cm -1 1 H-NMR (250 MHz, CDCl 3 ) δ(ppm): (m, 17H), (m, 4H), (m, 2H), (m, 2H), (m, 1H), 4.18 (q, J = 7.5 Hz, 2H, H-2), 5.52 (d, J = 1.2 Hz, 1H, one of H-5), 6.15 (d, J = 1.6 Hz, 1H, one of H-5); 13 C-NMR (62.5 MHz, CDCl 3 ) δ(ppm): 14.1 (C-1), 21.9, 22.2, 23.7, 23.9 S-15
16 (2 C), 24.0, 25.6, 25.9, 29.1, 33.4, 38.2 (C-6 and C-8 to C-17), 49.6 (C-7), 60.7 (C-2), (C-5), (C-4), (C-3), (C-18); MS (APCI) m/z (relative intensity): (M + +1) 295 (100 %); 250 (16 %); 249 (95 %); HRMS (EI+) : calculated mass for C 18 H 30 3 ( , [M] + ), found ( ). Adduct 6e Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 20:1 10:1 5:1) to give 33.6 mg (80%) of 6e as a colorless oil. Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 10:1 CH 2 Cl 2 :MeH = 100:1 ) to give 36.3 mg (86%) of 6e and 210 mg (4.9 equiv) of 5c H-NMR (300 MHz, CDCl 3 ) δ(ppm): 1.31 (t, J = 7.3 Hz, 3H, H-1), 2.13 (s, 3H, H-9), (m, 3H, H-10 and one of H6), 2.60 (dd, J = 14.0, 7.9 Hz, 1H, one of H-6), 2.88 (tt, J = 7.4, 6.4 Hz, 1H, H-7), 4.21 (q, J = 7.3 Hz, 2H, H-2), 5.02 (s, 1H, one of H-12), 5.07 (d, J = 7.0 Hz, 1H, one of H-12), 5.55 (s, 1H, one of H-5), (m, 1H, H-11), 6.19 (d, J = 0.9 Hz, 1H, one of H-5); 13 C-NMR (75 MHz, CDCl 3 ) δ(ppm): 14.4 (C-1), 30.3 (C-9), 33.7 (C-6), 35.7 (C-10), 51.0 (C-7), 61.0 (C-2), (C-12), (C-5), (C-11), (C-4), (C-3), (C-8). MS (APCI) m/z (relative intensity): (M + ) 210 (42 %), 165 (9 %), 138 (14 %), 106 (11 %), 85 (100 %), 84 (17 %), 65 (32 %), 60 (33 %). HRMS (ESI): calculated mass for C 12 H 19 3 ( , [M+H] + ), found ( ). Adduct 6f Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 20:1 10:1 5:1) to give 34.9 mg (83%) of 6f as a colorless oil. Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 10:1 CH 2 Cl 2 :MeH = 100:1 ) to give 38.2 mg (91%) of 6f and 236 mg (5.8 equiv) of 5c S-16
17 1 H-NMR (300 MHz, CDCl 3 ) δ(ppm): 1.31 (t, J = 7.1 Hz, 3H, H-1), (m, 2H, H-10), (m, 2H, H-9), (m, 4H, H-6 and H-7), 4.21 (q, J = 7.1 Hz, 2H, H-2), (m, 2H, H-12), 5.58 (s, 1H, one of H-5), (m, 1H, H-11), 6.17 (s, 1H, one of H-5); 13 C-NMR (75 MHz, CDCl 3 ) δ(ppm): 14.4 (C-1), 26.4 (C-10), 27.9 (C-6), 41.8 and 42.0 (C-7 and C-9), 60.9 (C-2), (C-12), (C-5), (C-11), (C-4), (C-3), (C-8); MS (APCI) m/z (relative intensity): (M + +1) 211 (100 %), 197 (26 %), 165 (77 %), 163 (42 %), 149 (52 %), 147 (29 %), 135 (33 %), 109 (32 %). HRMS (ESI): calculated mass for C 12 H 19 3 ( , [M+H] + ), found ( ). Adduct 6g Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 9:1 3:1) to give 37.2 mg (70%) of 6g as a colorless oil. Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 5:1 CH 2 Cl 2 :MeH = 100:1 ) to give 47.4 mg (89%) of 6g and 253 mg (6.1 equiv) of 5c IR: 2929 cm -1 (stretching C-H), 1707 cm -1 (C=), 1630 cm -1 (C=C-C=), 1444, 1370, 1189, 1146, 1108, 1024, 908, 734, 649 cm -1 1 H-NMR (300 MHz, CDCl 3 ) δ(ppm): 1.31 (t, J = 7.2 Hz, 3H, H-1), (m, 5H), (m, 2H), (m, 7H), (m, 1H, H-7), 4.20 (q, J = 6.9 Hz, 2H, H-2), 5.49 (d, J = 1.2 Hz, 1H, one of H-5), 6.16 (d, J = 1.5 Hz, 1H, one of H-5); 13 C-NMR (75 MHz, CDCl 3 ) δ(ppm): 14.2 (C-1), 20.9, 21.2 (C- 9 and C-13), 29.4, 34.4 (C-6 and C-8), 38.8, 43.4 (C-10, C-12 and-14), 51.2 (C-7), 60.9 (C-2), (C- 5), (C-4), (C-3), (C-11), (C-15); MS (ESI) m/z (relative intensity): (M + ) 266 (100 %); 249 (23 %), 244 (8 %), 115 (29 %), 83 (9 %); HRMS (EI+) : calculated mass for C 15 H 22 4 ( , [M] + ), found ( ). Adduct 6h Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 9:1 3:1) to give 37.6 mg (67%) of 6h as a colorless oil. Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 5:1 CH 2 Cl 2 :MeH = 100:1 ) to give 50.7 mg (90%) of 6h and 172 mg (4.2 equiv) of 5c. S-17
18 IR: 2935 cm -1 (stretching C-H), 1708 cm -1 (C=), 1629 cm -1 (C=C-C=), 1463, 1369, 1255, 1182, 1025, 949, 872, 819, 727 cm -1 1 H-NMR (250 MHz, CDCl 3 ) δ(ppm): 1.26 (t, J = 7.1 Hz, 3H, H-1), (m, 3H), (m, 2H), (m, 2H), (m, 2H), (m, 10H), 4.16 (q, J = 7.1 Hz, 2H, H-2), 5.45 (d, J = 1.2 Hz, 1H, one of H-5), 6.10 (s, 1H, one of H-5); 13 C-NMR (62.5 MHz, CDCl 3 ) δ(ppm): 14.1 (C-1), 17.3, 23.0, 24.3, 26.9, 29.3, 34.2, 38.6, 39.3, 42.2 (C-6, C-8 to C-12 and C-14 to C-16), 51.1 (C-7), 60.7 (C-2), (C-5), (C-4), (C-3), 214.0, (C-13 and C-17); MS (APCI) m/z (relative intensity): (M + ) 294 (11 %); 277 (100 %); 259 (11 %); 249 (17 %); 248 (20 %); 239 (40 %); 225 (21 %); HRMS (CI+) : calculated mass for C 17 H 26 4 ( , [M] + ), found ( ) Adduct 6i Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 20:1 10:1 5:1) to give 31.6 mg (63%) of 6i as a colorless oil. Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 10:1 CH 2 Cl 2 :MeH = 100:1 ) to give 39.7 mg (79%) of 6i and 186 mg (4.5 equiv) of 5c H-NMR (300 MHz, CDCl 3 ) δ(ppm): 1.29 (t, J = 7.1 Hz, 3H, H-1), (m, 6H, H-10 H-12), (m, 3H, H-9 and one of H-13), (m, overlapped, 1H, one of H-13), 2.53 (d, J = 14.0 Hz, 1H, one of H-6), 2.85 (d, J = 14.0 Hz, 1H, one of H-6), 4.18 (q, J = 7.2 Hz, 2H, H-2), (m, 2H, H-15), 5.56 (s, 1H, one of H-5), (m, 1H, H-14), 6.24 (d, J = 1.5 Hz, 1H, one of H-5); 13 C-NMR (75 MHz, CDCl 3 ) δ(ppm): 14.4 (C-1), 21.0 (C-11), 26.9 (C-10), 36.2 (C-13), 36.5 (C-9), 39.4 (C-6), 39.7 (C- 12), 52.0 (C-7), 61.1 (C-2), (C-15), (C-5), (C-14), (C-4), (C-3), (C- 8); MS (APCI) m/z (relative intensity): [M + +H] 251 (100 %), 252 (11%), 206 (9%), 205 (66%), 187 (13%), 163 (7%), 159 (11%); HRMS (ESI): calculated mass for C 15 H 23 3 ( , [M+H] + ); found ( ). S-18
19 Adduct 6j Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 20:1 10:1 5:1) to give 38.4 mg (72%) of 6j as a colorless oil. Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 10:1 CH 2 Cl 2 :MeH = 100:1 ) to give 48.5 mg (91%) of 6j and 214 mg (5.0 equiv) of 5c H-NMR (500 MHz, CDCl 3 ) δ(ppm): 0.87 (s, 9H, H-14), 1.28 (t, J = 7.1 Hz, 3H, H-1), 1.49 (td, J = 12.7, 4.5 Hz, 1H, H-11), (m, 3H, H-7 and H-12), 1.77 (ddd, J = 12.4, 6.5, 3.4 Hz, 1H, one of H-10), 1.98 (dddd, J = 12.2, 5.9, 3.0, 2.9 Hz, 1H, one of H-10), 2.31 (dt, J = 12.4, 3.0 Hz, 1H, one of H-9), 2.41 (dd, J = 13.7, 7.5 Hz, 1H, one of H-6), 2.73 (dt, J = 12.8, 5.7 Hz, 1H, one of H-9), 2.76 (dd, J = 14.0, 7.7 Hz, 1H, one of H-6), 4.18 (q, J = 7.1 Hz, 2H, H-2), 5.57 (s, 1H, one of H-5), 6.20 (s, 1H, on e of H-5); 13 C-NMR (125 MHz, CDCl 3 ) δ(ppm): 14.3 (C-1), 26.6 (C-10), 27.5 (C-14), 31.1 (C-12), 32.6 (C-13), 33.7 (C-6), 38.7 (C-9), 41.5 (C-11), 48.1 (C-7), 61.0 (C-2), (C-5), (C-4), (C-3), (C-8); MS (APCI) m/z (relative intensity): (M + +1) 266 (100 %), 267 (10%), 237 (54%), 205 (45%), 153 (15%); HRMS (ESI): C 16 H 26 Na 3 [M+Na + ] calculated mass ( ); found mass ( ). Adduct 6k Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 20:1 10:1 5:1) to give 9.8 mg (16%) of 6k as a colorless oil. Method C: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 10:1 CH 2 Cl 2 :MeH = 100:1 ) to give 33.7 mg (55%) of 6k H-NMR (500 MHz, CDCl 3 ) δ(ppm): 0.89 (s, 9H, H-14), 1.29 (t, J = 7.1 Hz, 3H, H-1), 1.47 (td, J = 12.5, 4.7 Hz, 1H, H-11), (m, 4H, H-12 and H-10), (m, 3H, H-9 and one of H-15), 2.42 (d, J = 13.9, 1H, one of H-6), (m, 1H, one of H-15), 2.81 (dd, J = 14.0, 1H, one of H-6), 4.18 (q, J = S-19
20 7.1 Hz, 2H, H-2), (m, 2H, H-17), 5.58 (s, 1H, one of H-5), (m, 1H, H-16), 6.25 (s, 1H, one of H-5); 13 C-NMR (125 MHz, CDCl 3 ) δ(ppm): 14.3 (C-1), 26.5 (C-10), 27.4 (C-14), 32.7 (C-13), 36.1 (C-12), 38.1 (C-6), 39.2 (C-9), 41.6 (C-11), 52.3 (C-7), 61.0 (C-2), (C-17), (C-5), (C- 16), (C-4), (C-3), (C-8); MS (APCI) m/z (relative intensity): (M + +1) 307 (100 %), 267 (21%), 209 (51%), 153 (42%), 113 (21%), 96 (9%); HRMS (ESI): C 19 H 30 Na 3 [M+Na + ] calculated mass ( ); found mass ( ). Adduct 6l Method A: The crude was purified by (φ1.5 cm, 9 cm of Si 2, 10 ml fracions; P.E : Et 2 = 100:0 9:1 3:1) to give 27.1 mg (46%) of syn-6l and 8.2 mg (14%) of anti-6l. Syn-6l IR: 2958, 2931 and 2872 cm -1 (stretching C-H), 1714 and 1695 cm -1 (C=), 1629 cm -1 (C=C-C=), 1465, 1370, 1272, 1202, 1095, 1026, 953, 861, 818, 736, 703 cm -1 1 H-NMR (250 MHz, CDCl 3 ) δ(ppm): 0.92 (d, J = 6.7 Hz, 3H, H-17), 1.26 (t, J = 7.1 Hz, 3H, H-1), (m, 6H, H-8, H-9 and H-10), (m, 2H, H-14), (m, 3H, one of each H-6, H-13 and H-15), (m, 2H, one of H-6 and H-11), (m, 3H, H-7 and one of each H-13 and H-15), 4.16 (q, J = 7.1 Hz, 2H, H-2), 5.47 (s, 1H, one of H-5), 6.10 (d, J = 1.6 Hz, 1H, one of H-5); 13 C-NMR (62.5 MHz, CDCl 3 ) δ(ppm): 14.1 (C-1), 14.7 (C-17), 17.8 (C-14), 20.7 (C-9), 30.2 (C-8), 31.9 (C-10), 33.0 (C-6), 37.9 (C-13), 40.2 (C-15), 47.0 (C-11), 51.5 (C-7), 60.7 (C-2), (C-5), (C-4), (C-3), (C-16), (C-12); MS (APCI) m/z (relative intensity): [M] (7 %), 277 (15%), 259 (46%), 249 (100%), 231 (95%), 213 (58%), 203 (30%), 195 (16%), 185 (38%); HRMS (EI + ) : calculated mass for C 17 H 26 4 ( , [M] + ); found mass ( ). Anti-6l IR: 2960, 2934 and 2874 cm -1 (stretching C-H), 1710 cm -1 (C=), 1629 cm -1 (C=C-C=), 1446, 1370, 1328, 1305, 1179, 1148, 1054, 915, 733 cm -1 1 H-NMR (300 MHz, CDCl 3 ) δ(ppm): 0.80 (d, J = 7.2 Hz, 3H, H-17), (m, 3H), 1.27 (t, J = 7.0 Hz, 3H, H-1), (m, 3H), (m, 2H), (m, 1H), (m, 1H), (m, 2H), (m, 2H), 4.14 (q, J = 7.0 Hz, 2H, H-2), 5.47 (s, 1H, one of H-5), 6.10 (d, J = 0.9 Hz, 1H, S-20
21 one of H-5); 13 C-NMR (75 MHz, CDCl 3 ) δ(ppm): 14.0, 14.1 (C-1 and C-17), 16.9, 22.4, 24.7, 32.2, 35.5, 38.0, 39.4 (C-6, C-8 to C-10 and C-13 to C-15), 39.4 (C-11), 61.0 (C-7), 67.7 (C-2), (C-5), (C-4), (C-3), (C-12 and C-16); MS (APCI) m/z (relative intensity): [M] (12 %); 277 (67 %); 259 (18 %); 249 (39 %); 231 (100 %); 213 (55 %); 203 (18 %); 195 (8 %); 185 (21 %). HRMS (EI + ) : calculated mass C 17 H 26 4 ( , [M] + ); found mass ( ). I. Structural data for Table 3 : B3LYP/6-311+G(d,p) geometries (Cartesian coordinates, all values in Å) C C H H H C H H E(UB3LYP) = a.u. S-21
22 C C C C C H H H H H H H E (UB3LYP= a.u. S-22
23 C C C C C C H H H H H H H H H E (UB3LYP) = a.u. S-23
24 II. Structural data for Table S-3 : B3LYP/6-31+G(d) geometries (Cartesian coordinates, all values in Å) C C H C H H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-24
25 C C C C C H H H H H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-25
26 C C C C H H C H C H H H H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-26
27 H 3 C-CH=CH 2 : H C C H H C H H H E(RB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-27
28 H 3 C-CH=CH 2 : H C C H H C H H H E(RB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-28
29 H 3 CC-CH=CH 2 : H C C H H C C H H H E(RB+HF-LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-29
30 1. Addition of to H 3 C-CH=CH 2 (a) Transition state: C C H H C C H H C H H H C H H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-30
31 (b) Product: C C H H C C H H C H H H C H H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-31
32 2. Addition of to H 3 C-CH=CH 2 (a) Transition state: C C H H C C H H C H H H H C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-32
33 (b) Product: C C H H C C H H C H H H H C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-33
34 3. Addition of to H 3 CC CH=CH 2 (a) Transition state: C C H H C C H H C C H H H C H H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-34
35 (b) Product: C C H H C C H H C C H H H C H H H H E(UB+HF LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-35
36 4. Addition of to H 3 C CH=CH 2 (a) Transition state: C C C C C H H H H H H H H C C H H C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-36
37 (b) Product: C C C C C H H H H H H H H C C H H C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-37
38 5. Addition of to H 3 C CH=CH 2 (a) Transition state: C C C C C H H H H H H H H C C H H C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-38
39 (b) Product: C C C C C H H H H H H H H C C H H C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-39
40 6. Addition of to H 3 CC CH=CH 2 (a) Transition state: C C C C C H H H H H H H H C C H H C C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-40
41 (b) Product: C C C C C H H H H H H H H C C H H C C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-41
42 7. Addition of to H 3 C CH=CH 2 (a) Transition state: H C C H H C C C C H H C H C H H H H H H C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-42
43 (b) Product: H C C H H C C C C H H C H C H H H H H H C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-43
44 8. Addition of to H 3 C CH=CH 2 (a) Transition state: H C C H H C C C C H H C H C H H H H H H C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-44
45 (b) Product: H C C H H C C C C H H C H C H H H H H H C H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-45
46 9. Addition of to H 3 CC CH=CH 2 (a) Transition state: H C C H H C C H H H C C C C H H C H C H H H H H H E(UB3LYP) = a.u. Zero Point Vibrational Energy = a.u. H(298.15K) = a.u. S-46
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