Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003
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- Βλάσιος Παπαγεωργίου
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1 Supporting Information for Angew. Chem. Int. Ed. Z51732 Wiley-VCH Weinheim, Germany
2 SM 1 Equilibrium and Kinetic euterium Isotopic Effects on the Hetero-iels-Alder Addition of Sulfur ioxide** Frédéric Monnat, [a] Pierre Vogel [a] *, Rubén Meana and José A. Sordo [b] * [a] Prof. r. P. Vogel, r. F. Monnat Institute of Molecular and Biological Chemistry, Swiss Institute of Technology, BCH CH-1015 Lausanne-origny (Switzerland) Fax: (+41) ; pierre.vogel@epfl.ch. [b] Prof. r. José A. Sordo, Mr. Rubén Meana Laboratorio de Química Computacional, epartamento de Química Física y Analítica, Universidad de Oviedo, Oviedo, Principado de Asturias (Spain) Fax: (+34) ; jasg@correo.uniovi.es
3 SM 2 General. Reagents and solvents are from Fluka, Buchs, Switzerland. Solvents are distilled before use. Anhydrous THF and Et 2 O are distilled from Na/benzophenone, CH 2 Cl 2 from CaH 2. Sulfur dioxide was dried by a column of basic alumina 90 (Merck, activity I). Kinetic measurements and NMR tube preparations for the reactions with sulfur dioxide, see [F. Monnat, P. Vogel, J. A. Sordo, Helv. Chim. Acta 2002, 85, 712]. Spectral recording, see [K. Kraehenbuehl, S. Picasso, P. Vogel, Helv. Chim. Acta 1998, 81, 1439]. cis-(3,3-2 H 2 )-3a,4,5,6,7,7a-Hexahydro-2-benzofuran-1(3H)-one (8). A suspension of NaB 4 (5 g, mol, 98 atom %, Fluka) in anhydrous tetrahydrofuran (THF, 23 ml), was added dropwise to a stirred solution of cis-cyclohexane-1,2- dicarboxylic anhydride (18.4 g, mol) in anhydrous THF (120 ml) cooled to 0 C and under Ar atmosphere. The white suspension is then stirred at 20 C for 2 days and 5 M aqueous HCl (50 ml) was added slowly at 0 C. Water (60 ml) was added and the mixture extracted with Et 2 O (90 ml, 4 times). The combined ethereal extracts were washed with H 2 O (100 ml, twice), dried (MgSO 4 ) and the solvent was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel (light petroleum ether/acoet
4 SM 3 2:1), giving a colorless oil (13.8 g, 81%), b.p. 100 C (1 Torr). UV (CH 3 CN) λ max : 212 (ε = 300). IR (film) ν: 2935, 2885, 2855, 1780, 1450, 1360, 1330, 1210, 1120, 1045, 990, 980, 915, 855 cm H-NMR (400 MHz, CCl 3 ) δ H : (m, H- C(7a)), (m, H-C(3a)), (m, H a -C(7)), (m, H a -C(4)), (m, H b -C(7), H a -C(6), et H a - C(5)), (m, H b -C(4), H b -C(6), H b -C(5)). Signals at δ H 4.2 & 3.92 ppm show less than 2% of H. 13 C-RMN (100.6 MHz, CCl 3 ) δ C : (s, C(1)), 71.1 (quint, 1 J(C,)=22, C(3)), 39.4 (d, 1 J(C,H)=126, C(7a)), 35.2 (d, 1 J(C,H)=135, C(3a)), 27.1 (t, 1 J(C,H)=128, C(4)), 23.4 (t, 1 J(C,H)=128, C(5)), 22.9 (t, 1 J(C,H)=128, C(7)), 22.5 (t, 1 J(C,H)=128, C(6)). 2 H- NMR (61.4 MHz, CCl 3 ) δ : 4.20 (s, a -C(3)), 3.95 (s, b - C(3)). CI-MS (NH 3 ) m/z: 143 ([M+H + ], 7), 142 (M +, 7), 97 ([M+H + -CO 2 ], 27), 83 (85), 81 (100). Anal. calcd. for C 8 H 10 2 O 2 (142.19): H 7.09, C 67.58; found: H 7.20, C cis-cyclohexane-1,2-(α,α- 2 H 2 )-dimethanol (9). Lactone 8 (3 g, 21.1 mmol) was added portionwise to a stirred suspension of LiAlH 4 (1.6 g, 42.2 mmol) in anhydrous THF (44 ml) under Ar atmosphere. The mixture was stirred at 20 C for 1 h and a saturated aqueous solution of NH 4 Cl (12 ml) was added
5 SM 4 portionwise. Et 2 O (30 ml), then H 2 O (10 ml) were added. The precipitate was taken off by filtration on Celite, rinsing with Et 2 O. The solvent was evaporated in vacuo yielding a white solid (2.92 g, 95%), m.p C. UV (CH 3 CN) λ max : 192 (ε = 200). IR (KBr) ν: 3340, 2925, 2860, 1450, 1355, 1145, 1095, 1075, 1040, 1025, 970, 675 cm H-NMR (400 MHz, CCl 3 ) δ H : 3.79 (dd, 2 J(H a -C(α'), H b -C(α'))=11.0, 3 J(H a -C(α'), H- C(2))=8.0, H a -C(α')), 3.60 (dd, 2 J(H a -C(α'), H b -C(α'))=11.0, 3J(H a -C(α'), H-C(2))=4.0, H b -C(α')), 2.29 (s, H-OC(α), H-O C(α')), 1.95 (m, H-C(1), H-C(2)), (m, H 2 -C(3), H 2 - C(4), H 2 -C(5), H 2 -C(6)). 13 C-NMR (100.6 MHz, CCl 3 ) δ C : 63.8 (t, 1 J(C,H)=140, C(α')), 63.0 (quint, 1 J(C,)=21, C(α)), 39.7 (d, 1 J(C,H)=129, C(2)), 39.6 (d, 1 J(C,H)=129, C(1)), 27.0 (d, 1J(C,H)=125, C(3), C(6)), 23.9 (t, 1 J(C,H)=127, C(4), C(5)). 2 H-NMR (61.4 MHz, CCl 3 ) δ : 3.75 (s, a -C(α)), (s, b - C(α)). CI-MS (NH 3 ) m/z: 147 ([M+H + ], 0.3), 128 ([M-H-OH] +, 3), 111 ([M+H + -2 H-2 OH], 23), 98 (83), 96 (86), 81 (100). Anal. calcd. for C 8 H 14 2 O 2 (146.22): H 9.65, C 65.71; found: H 9.41, C
6 SM 5 cis-cyclohexane-1,2-(α,α- 2 H 2 )-dimethyl bis(paratoluenesulfonate) (10). A solution of diol 9 (5.97 g, 40.8 mmol) in anhydrous pyridine (26 ml) was added dropwise to a stirred mixture of paratoluenesulfonyl chloride (24.4 g, 120 mmol), 4-dimethylaminopyridine (0.781 g, 6.4 mmol) in anhydrous pyridine (20 ml) cooled to 0 C and under Ar atmosphere. After stirring at 20 C for 25 min, H 2 O (40 ml) was added and the mixture stirred at 20 C for 20 min. The precipitate was collected (Büchner filter), washed with H 2 O, then with MeOH. It was then dried in vacuo, yielding a white solid (12.9 g, 69%), m.p C. UV (CH 3 CN) λ max : 272 (ε = 2100), 261 (2500), 224 (22'900), 200 (15'900). IR (KBr) ν: 3035, 2930, 2860, 1600, 1450, 1350, , 960, 940, 820, 665, 555 cm H-NMR (400 MHz, CCl 3 ) δ H : 7.77 (d, 3 J(H-C(3'), H- C(2'))=8.0, 4 H-C(2')), 7.37 (d, 3 J(H-C(3'), H-C(2'))=8.0, 4 H-C(3')), 3.91 (d, 3 J(H-C(1), H-C(α'))=7.0, H 2 -C(α')), 2.47 (s, 2 Me), 2.04 (m, H-C(1), H-C(2)), (m, H 2 -C(3), H 2 -C(4), H 2 -C(5) et H 2 -C(6)). 13 C-NMR (100.6 MHz, CCl 3 ) δ C : (s, 2C(4')), (s, 2C(1')), (d, 1 J(C,H)=161, 4C(3')), (d, 1J(C,H)=166, 4C(2')), 70.3 (t, 1J(C,H)=148, C(α')), 69.6 (quint, 1 J(C,)=22, C(α)), 36.4 (d, 1J(C,H)=130, C(2)), 36.2 (d, 1 J(C,H)=130, C(1)), 25.7 (t,
7 SM 6 1J(C,H)=128, C(3)), 25.6 (t, 1 J(C,H)=128, C(6)), 22.8 (t, 1J(C,H)=129, C(4)), 22.7 (t, 1 J(C,H)=129, C(5)), 21.6 (q, 1J(C,H)=127, 2 Me). 2 H-NMR (61.4 MHz, CCl 3 ) δ : 3.90 (s, 2 - C(α)). CI-MS (NH 3 ) m/z: 472 ([M+NH + 4 ], 100), 471 ([M+NH 3 ] +, 69), 454 ([M] +, 0.6), 283([M-OTs] +, 19), 155 (Ts +, 8), 112 ([M-2 OTs] +, 6), 111 (56), 110 (32). Anal. calcd. for C 22 H 26 2 O 6 S 2 (454.59): H 5.76, C 58.13; found: H 5.73, C [( 2 H 2 )-Methylidene]-2-methylidenecyclohexane (3). Bistosylate 10 (7.2 g, 15.8 mmol) was added portionwise to a stirred solution of t-buok (7.1 g) in anhydrous MSO (63 ml). After stirring at 25 C for 35 min, the mixture was cooled to 0 C and H 2 O (60 ml) was added. The mixture was extracted with pentane (50 ml, 3 times). The combined extracts were washed with saturated aqueous solution of NH 4 Cl (20 ml, twice) and dried (MgSO 4 ). Solvent distillation at 1 atmosphere, then distillation of the residue under reduced pressure, b.p. 30 C (600 mbar). The crude diene 3 is then redistilled with a Vigreux column, b.p C (80 mbar), colorless liquide (900 mg, 52%). UV (CH 3 CN) λ max : 221 (ε = 4000). IR (film) ν: 3080, 2935, 2885, 2860, 2840, 1630, 1595, 1440, 1260, 1100, 1020, 890, 820, 805, 740, 715 cm H-NMR
8 SM 7 (400 MHz, C 2 Cl 2 ) δ H : 4.94 (dm, 2 J(H cis -C(2'), H trans C(2'))=2.6, H cis -C(2')), 4.67 (dm, 2 J(H cis -C(2'), H trans C(2'))=2.6, H trans - C(2')), (m, H 2 -C(3), H 2 -C(6)), (m, H 2 - C(4), H 2 -C(5)). 13 C-NMR (100.6 MHz, C 2 Cl 2 ) δ C : (s, C(2)), (s, C(1)), (t, 1 J(C,H)=156, C(2 )), (quint, 1 J(C,)=24, C(1 )), 35.7 (t, 1 J(C,H)=126, C(3)), 35.6 (t, 1 J(C,H)=126, C(6)), 27.2 (2 t quint, 1 J(C,H)=128, 2J(C,H)=5, C(4), C(5)). 2 H-NMR (61.4 MHz, CCl 3 ) δ : 4.97 (s, cis -C(1')), 4.70 (s, trans -C(1')). GC-CI-MS (NH 3 ) m/z: 128 ([M+NH + 4 ], 10), 111 ([M+H + ], 100), 110 (M +, 32), 95 (6), 79 (2). (4,4-2 H 2 )-1,4,5,6,7,8-Hexahydro-2,3-benzoxathiine-3-oxide (4), (1,1-2 H 2 )-1,4,5,6,7,8-hexahydro-2,3-benzoxathiine-3-oxide (5) and (1,1-2 H 2 )-1,3,4,5,6,7-hexahydrobenzo[c]thiophene 2,2- dioxide (6). A mixture of diene 3 (11.6 mg, 0.21 molar), anhydrous sulfur dioxide (233 mg, 7.31 molar) in CCl 2 (total volume of 0.5 ml) was made in a 5 mm pyrex NMR tube (vac. line, bulb-to-bulb distillation, liquid N 2 ). The NMR tube was left at 75 C. After 780 min ( 1 H-NMR) 99% conversion was reached and a 51.4/46.5/2.1 mixture of 4, 5 and 6 was formed.
9 SM 8 Sultines 4 and 5 are equilibrated first and then converted into 6 in a few minutes at 40 C. ata for 4: 1 H-NMR (400 MHz, C 2 Cl 2 /CFCl 3 /SO 2, 213K) δ H : 4.27 (d, 3 J(H a -C(1), H b -C(1))=15.8, H a -C(1)), 4.12 (d, 3 J(H a -C(1), H b -C(1))=15.8, H b -C(1)), (m, H 2 -C(5)), (m, H 2 -C(8)), (m, H a -C(6), H a -C(7)), (m, H b - C(6), H b -C(7)). 13 C-NMR ( MHz, C 2 Cl 2 /CFCl 3 /SO 2, 213K) δ C : (s, C(8a)), (s, C(4a)), 60.0 (t, 1 J(C,H)=150, C(1)), 49.0 (quint, 1 J(C,)=20, C(4)), 29.0 (t, 1 J(C,H)=127, C(5)), 24.8 (t, 1 J(C,H)=127, C(8)), 22.1 (t, 1 J(C,H)=129, C(6)), 21.4 (t, 1 J(C,H)=127, C(7)). 2 H-NMR (61.4 MHz, C 2 Cl 2 /CFCl 3 /SO 2, 203K) δ : 3.38 (br. s, a -C(4)), 2.72 (br. s, b -C(4)). 17 O-NMR (54.2 MHz, C 2 Cl 2 /CFCl 3 /SO 2, 213K) δ 17O : 133 (br. s, ν ½ =1080, O=S(3)), 77 (br. s, ν ½ =1790, O(2)). ata for 5: 1 H-NMR (400 MHz, C 2 Cl 2 /CFCl 3 /SO 2, 213K) δ H : 3.40 (dm, 3 J(H a -C(4), H b -C(4))=17.0, H a -C(4)), 2.73 (dm, 3 J(H a -C(4), H b -C(4))=17.0, H b -C(4)), (m, H 2 -C(5)), (m, H 2 -C(8)), (m, H a -C(6), H a -C(7)), (m, H b - C(6), H b -C(7)). 13 C-NMR ( MHz, C 2 Cl 2 /CFCl 3 /SO 2, 213K) δ C : (s, C(8a)), (s, C(4a)), 59.3 (quint, 1J(C,)=22, C(1)), 49.6 (t, 1 J(C,H)=137, C(4)), 29.1 (t,
10 SM 9 1J(C,H)=127, C(5)), 24.8 (t, 1 J(C,H)=127, C(8)), 22.1 (t, 1J(C,H)=129, C(6)), 21.4 (t, 1 J(C,H)=127, C(7)). 2 H-NMR (61.4 MHz, C 2 Cl 2 /CFCl 3 /SO 2, 203K) δ : 4.24 (br. s, a -C(1)), 4.11 (br. s, b -C(1)). 17 O-NMR (54.2 MHz, C 2 Cl 2 /CFCl 3 /SO 2, 213K) δ 17O : 133 (br. s, ν ½ =1080, O=S(3)), 77 (br. s, ν ½ =1790, O(2)). Example of kinetic measurements 3 + (SO 2 ) SO SO 2 diene 3: sultine 1: 4, sultine 2: 5, sulfolene: T = -54 C conc [mol/dm 3 ] diene sultine 1 sultine sulfolene time [min]
11 SM T = -54 C 0.25 conc [mol/dm 3 ] sultine 2 sultine sulfolène 0.00 diène time [min] Simulation of the kinetics 3 + (SO 2 ) SO SO T = -54 C sulfolène conc [mol/dm 3 ] sultine 1 sultine diène temps 10 3 [min] 13 C-NMR spectrum of SO
12 SM SO 2-75 C S O O + S O O + S O O peak 1/T2 1: e+001 ± 1.17e+000 2: e+001 ± 4.54e-001 peak height 1: e+003 ± 4.03e+002 2: e+004 ± 3.57e+002 rel. integrals (%) 1: / : / toluene dienes (1+3) dienes (1+3) sultines ppm
13 SM 12 Kinetics of the disappearence of dienes at 75 C, [SO 2 ] o = 2.76 moldm -3, [1] o = 0.21 moldm -3, [3] o = 0.11 moldm conc [mol/dm 3 ] time [min]
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