Supporting Information for Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Changkun Li and Jianbo Wang* Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China R Ο NH CCl 3 + Ar-H BF 3 OEt 2 (30 mol %) rt, 5 min 41-90 % R Ar Contents 1) General S2 2) Spectral data for 3-phenylprop-2-yn-1-yl trichloroacetimidates 2b-k, 6, 11, 12... S2 3) Spectra data for 1,3-diphenylprop-1-ynes 3c-k, 5a-h, 13.... S4 4) Reference S7 5) Spectral for 3-phenylprop-2-yn-1-yl trichloroacetimidates.. S8 6) Spectra for 1, 3-diphenylprop-1-ynes.. S22 S1
General. All reactions with air- and moisture-sensitive components were performed under a nitrogen atmosphere in a flame-dried reaction flask. All solvents were distilled prior to use. CH 2 Cl 2 was freshly distilled from CaH 2 and benzene was freshly distilled from Na before use. For chromatography, 200-300 mesh silica gel was employed. 1 H and 13 C NMR spectra were recorded at 200 and 50 MHz, or 300 and 75 MHz. Chemical shifts are reported by ppm using tetramethylsilane as internal standard. Substituent propargyl alcohols were prepared by cross-coupling reactions of corresponding aryl halides and propargyl alcohol following the literature procedure. 1 Spectral data for 3-phenylprop-2-yn-1-yl trichloroacetimidates 2b-k, 6, 11, 12. NH Ο CCl 3 3-p-Tolylprop-2-ynyl trichloroacetimidate (2b): 96 %; white solid; m.p. 45-46 o C; 1 H NMR (300 MHz, CDCl 3 ) δ 8.50 (s, 1H), 7.37 (d, J = 8.1 Hz, 2H), 7.12 (d, J = 8.1 Hz, 2H), 5.14 (s, 2H), 2.34 (s, 3H); 13 C NMR (75 MHz CDCl 3 ) δ 161.9, 138.9, 131.8, 129.0, 118.9, 90.9, 87.3, 81.6, 57.1, 21.4; IR (neat, cm -1 ) 3343 (w), 2230(w), 1667 (s), 1292 (s), 1070(s); HRMS calcd for C 12 H 10 NOCl 3 288.9828, found: 288.9829. CH 3 NH Ο CCl 3 3-o-Tolylprop-2-ynyl trichloroacetimidate (2c): 84 %; light yellow oil; 1 H NMR (300 MHz, CDCl 3 ) δ 8.51(s, 1H), 7.43-7.41 (m, 1H), 7.23-7.12(m, 3H), 5.17 (s, 2H), 2.41(s, 3H); 13 C NMR (75 MHz CDCl 3 ) δ 161.8, 140.6, 132.1, 129.4, 128.7, 125.5, 121.8, 90.9, 86.1, 57.5, 20.6; IR (neat, cm -1 ) 3342 (w), 2237(w), 1663 (s), 1288 (s); HRMS calcd for C 12 H 10 NOCl 3 288.9828, found: 288.9826. NH 3-(p-Methoxyphenyl)prop-2-ynyl trichloroacetimidate (2d): 96 Ο CCl 3 %; light yellow oil; 1 H NMR (300 MHz, CDCl 3 ) δ 8.50 (s, 1H), 7.42 (d, J = 9.0 Hz, 2H), 6.84 (d, J = 9.0 Hz, 2H), 5.14 (s, 2H), 3.81 (s, 3H); 13 C NMR (75 MHz CDCl 3 ) δ 162.0, 160.0, 133.5, 114.1, MeO 113.9, 91.0, 87.2, 80.9, 57.7, 55.3; IR (neat, cm -1 ) 3340 (w), 2228(w), 1667 (s), 1510 (s),1290(s); HRMS calcd for C 12 H 10 NO 2 Cl 3 304.9777, found: 304.9763. O 2 N 319.9520. NH Ο CCl 3 3-(p-Nitrophenyl)prop-2-ynyl trichloroacetimidate (2e): 90 %; white solid; m.p. 132-133 o C; 1 H NMR (300 MHz, CDCl 3 ) δ 8.58 (s, 1H), 8.21(d, J = 9.0 Hz, 2H), 7.63 (d, J = 9.0 Hz, 2H), 5.19 (s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 161.8, 147.4, 132.7, 128.8, 123.5, 90.7, 87.5, 85.1, 57.0; IR (neat, cm -1 ) 3319 (m), 1664 (s), 1593 (m), 1510 (s), 1342 (s); HRMS calcd for C 11 H 7 N 2 O 3 Cl 3 319.9522, found: S2
Br NH Ο CCl 3 3-(p-Bromophenyl)prop-2-ynyl trichloroacetimidate (2f): 98 %; white solid; m.p. 53-54 o C; 1 H NMR (300 MHz, CDCl 3 ) δ 8.53(s, 1H), 7.46(d, J = 8.4Hz, 2H), 7.34(d, J = 8.4 Hz, 2H), 5.14(s, 2H); 13 C NMR (50 MHz CDCl 3 ) δ 161.8, 133.3, 131.5, 123.2, 121.0, 90.8, 86.1, 83.4, 57.4; IR (neat, cm -1 ) 3342 (w), 2242 (w), 1667 (s), 1287 (s), 1070 (s); HRMS calcd for C 11 H 7 NOCl 3 Br 352.8777, found: 352.8775. COOMe 332.9728. NH Ο CCl 3 Methyl 2-(3-trichloroacetimidoxyprop-1-ynyl) benzoate (2g): 90 %; light yellow oil; 1 H NMR (300 MHz, CDCl 3 ) δ 8.53 (s, 1H), 7.95(m, 1H), 7.60-7.40 (m, 3H), 5.21 (s, 2H), 3.93 (s, 3H); 13 C NMR (75MHz CDCl 3 ) δ 166.5, 161.9, 134.3, 132.1, 131.6, 130.3, 128.4, 122.5, 90.9, 87.2, 85.8, 57.6, 52.2; IR (neat, cm -1 ) 3342 (w), 1730 (s), 1668 (s), 1291 (s); HRMS calcd for C 13 H 10 NO 3 Cl 3 332.9726, found: 3-(3-Formylphenyl)prop-2-ynyl trichloroacetimidate (2h): 82 %; NH white solid; m.p. 61-63 o C; 1 H NMR (300 MHz, CDCl 3 ) δ 10.00 (s, Ο Ο CCl 1H), 8.58 (s, 1H), 7.98-7.48 (m, 4H), 5.17 (s, 2H); 13 3 C NMR H (75MHz CDCl 3 ) δ 191.2, 161.7, 137.3, 136.3, 133.1, 129.4, 129.0, 123.2, 90.7, 85.5, 83.9, 57.1; IR (neat, cm -1 ) 3340 (w), 2229 (w), 1701 (s), 1668 (s), 1284 (s), 1070 (s); HRMS calcd for C 12 H 8 NO 2 Cl 3 302.9621, found: 302.9623. 324.9825. NH Ο CCl 3 3-(Naphthalen-1-yl)prop-2-ynyl trichloroacetimidate (2i): 97 %; yellow solid; m.p. 34-35 o C; 1 H NMR (300 MHz, CDCl 3 ) δ 8.58 (s, 1H), 8.37-8.32 (m, 1H), 7.84-7.38(m, 6H), 5.30 (s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 161.9, 133.3, 133.0, 130.9, 129.3, 128.2, 126.9, 126.4, 126.0, 125.1, 119.7, 90.9, 87.1, 85.3, 57.6; IR (neat, cm -1 ) 3340 (w), 2233 (w), 1667 (s), 1289 (s); HRMS calcd for C 15 H 10 NOCl 3 324.9828, found: NH O S Ο CCl 3 H 308.9185, found: 308.9183. 3-(5-Formylthiophen-2-yl)prop-2-ynyl trichloroacetimidate (2j): 96 %; white solid; m.p. 69-70 o C; 1 H NMR (300 MHz, CDCl 3 ) δ 9.88 (s, 1H), 8.58 (s, 1H), 7.66 (d, J = 3.9Hz, 1H), 7.32 (d, J = 3.9 Hz, 1H), 5.19(s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 182.3, 161.7, 144.5, 135.6, 133.6, 131.1, 90.8, 90.6, 79.5, 57.0; IR (neat, cm -1 ) 3338 (w), 1667 (s), 1449 (s), 1287 (s), 1070 (s); HRMS calcd for C 10 H 6 NO 2 SCl 3 NH Ο CCl 3 Hept-2-ynyl trichloroacetimidate (2k): 97 %; light yellow oil; 1 H NMR (300 MHz, CDCl 3 ) δ 8.46 (s, 1H), 4.93 (t, J = 2.4 Hz, 2H), 2.30-2.24 (m, 2H), 1.56-1.39 (m, 4H), 0.93 (t, J = 7.2 Hz, 3H); 13 C NMR (75 MHz CDCl 3 ) δ 161.9, 91.0, 88.4, 73.3, 57.5, 30.3, 21.8, 18.4, 13.5; IR (neat, cm -1 ) 3346 (w), 2958 (w), 2237 (w), 1667 (s), S3
1289 (s), 1072 (s); HRMS calcd for C 9 H 12 NOCl 3 254.9985, found: 254.9975. NH O CCl 3 4,4-Dimethyl-1-phenylpent-1-yn-3-yl trichloroacetimidate (6): 87 %; colorless oil; 1 H NMR (300 MHz, CDCl 3 ) δ 8.46 (s, 1H), 7.47-7.44 (m, 2H), 7.31-7.29 (m, 3H), 5.37 (s, 1H), 1.17 (s, 9H); 13 C NMR (75MHz CDCl 3 ) δ 161.8, 131.9, 128.5, 128.2, 122.5, 91.5, 86.3, 84.5, 77.4, 36.1; IR (neat, cm -1 ) 3346 (w), 2970 (m), 2217 (w), 1666 (s); HRMS calcd for C 15 H 16 NOCl 3 331.0298, found: 331.0292. O HN CCl 3 2,2,2-Trichloro-N-(1,3-diphenylprop-2-ynyl)acetamide (11): 1 H NMR (300 MHz, CDCl 3 ) δ 7.63-7.19(m, 11H), 6.18 (d, J = 12.9 Hz, 1H); 13 C NMR (75MHz CDCl 3 ) δ 160.9, 137.3, 131.9, 129.0, 128.8, 128.4, 127.4, 127.1, 121.9, 92.2, 86.3, 84.9, 47.4; IR (neat, cm -1 ) 3320 (w), 2229 (w), 1701 (s), 1504 (s), 1492 (s); HRMS calcd for C 17 H 12 ONCl 3 350.9985, found: 350.9986. NH O CCl 3 1-Phenylprop-2-ynyl trichloroacetimidate (12): 2 61 %; white solid; m.p. 33-34 o C; 1 H NMR (300 MHz, CDCl 3 ) δ 8.60 (s, 1H), 7.63-7.59 (m, 2H), 7.38-7.43 (m, 3H), 6.56 (d, J = 2.1Hz, 1H), 2.72 (d, J = 2.1Hz, 1H); 13 C NMR (75 MHz CDCl 3 ) δ 161.2, 135.9, 129.1, 128.6, 127.4, 90.9, 79.5, 76.2, 69.8. Spectra data for 1,3-diphenylprop-1-ynes 3c-k, 5a-h, 13. 1-(3-o-Tolylprop-2-ynyl)benzene (3c): 1 H NMR (300 MHz, CDCl 3 ) δ 7.43-7.09(m, 9H), 3.86(s, 2H), 2.44(s, 3H); 13 C NMR (75MHz CDCl 3 ) δ 140.0, 136.9, 131.9, 129.3, 128.5, 127.9, 127.7, 126.5, 125.4, 123.4, 91.3, 81.6, 25.9, 20.8; IR (neat, cm -1 ) 3028 (w), 1604 (w), 1494 (m); HRMS calcd for C 16 H 14 206.1096, found: 206.1090. O 2 N 1-(3-(p-Nitrophenyl)prop-2-ynyl)benzene (3e): yellow solid; m.p. 45-46 o C; 1 H NMR (300 MHz, CDCl 3 ) δ 8.17-8.14 (m, 2H), 7.58-7.54 (m, 2H), 7.42-7.25 (m, 5H), 3.87 (s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 146.8, 135.8, 132.3, 130.6, 128.7, 127.9, 126.9, 123.5, 93.6, 81.0, 25.8; IR (neat, cm -1 ) 2916 (w), 2223 (w), 1593 (m), 1517 (s), 1342 (s); HRMS calcd for C 15 H 11 NO 2 237.0790, found: 237.0788. Br 1-(p-Bromophenyl)-3-phenylpropyne (3f) 1 H NMR (300 MHz, CDCl 3 ) δ 7.45-7.26 (m, 9H), 3.81 (s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 136.4, 133.1, 131.4, 128.6, 127.9, 126.7, 122.6, 121.9, 88.8, 81.6, 25.7; IR (neat, cm -1 ); 3029 (w), 1603 (w), 1486 (s), 1095 (m), 1011 (m), 823 (s), 726 (s), 691 (s); HRMS calcd for C 15 H 11 Br 270.0044, found: 270.0045. S4
COOMe Methyl 2-(3-phenylprop-1-ynyl)benzoate (3g): 1 H NMR (300 MHz, CDCl 3 ) δ 7.91 (d, J = 7.8 Hz, 1H), 7.55-7.32 (m, 8H), 3.90 (s, 2H), 3.84 (s, 3H); 13 C NMR (75 MHz CDCl 3 ) δ 166.8, 136.6, 134.2, 131.9, 131.5, 130.1, 128.4, 127.9, 127.4, 126.5, 123.9, 92.9, 81.2, 52.0, 26.0; IR (neat, cm -1 ) 2950 (w), 2230 (w), 1731 (s), 1593 (m), 1293 (s); HRMS calcd for C 17 H 13 O 2 [(M-H) + ] 249.0916, found: 249.0914. H O 3-(3-Phenylprop-1-ynyl)benzaldehyde (3h): 1 H NMR (300 MHz, CDCl 3 ) δ 9.96 (s, 1H), 7.93-7.25 (m, 9H), 3.83 (s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 191.6, 137.2, 136.3, 136.2, 132.9, 128.9, 128.6, 127.9, 126.7, 124.8, 89.4, 81.2, 25.6; IR (neat, cm -1 ) 2237 (w), 1700 (s); HRMS calcd for C 16 H 12 O 220.0888, found: 220.0886. 1-(3-Phenylprop-1-ynyl)naphthalene (3i): 1 H NMR (300 MHz, CDCl 3 ) δ 8.38 (d, J = 8.1 Hz, 1H), 7.81-7.24 (m, 11H), 3.96 (s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 136.7, 133.5, 133.1, 130.2, 128.6, 128.2, 127.9, 126.6, 126.6, 126.2, 125.2, 121.3, 92.5, 80.7, 26.0; IR (neat, cm -1 ) 3059 (w), 2217 (w), 1586 (w), 1495 (m); HRMS calcd for C 19 H 14 242.1096, found: 242.1092. H O S 5-(3-Phenylprop-1-ynyl)thiophene-2-carbaldehyde (3j): 1 H NMR (300 MHz, CDCl 3 ) δ 9.81(s, 1H), 7.59 (d, J = 3.9 Hz, 1H), 7.35-7.26 (m, 5H), 7.19 (d, J = 3.9 Hz, 1H), 3.85 (s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 182.3, 143.2, 136.0, 135.4, 133.3, 132.1, 128.6, 127.9, 126.9, 97.2, 75.3, 26.0; IR (neat, cm -1 ) 2226 (w), 1668 (s), 1448 (s), 1216 (m); HRMS calcd for C 14 H 10 OS 226.0452, found: 226.0456. 1-(Hept-2-ynyl)benzene (3k): 1 H NMR (300 MHz, CDCl 3 ) δ 7.37-7.19 (m, 5H), 3.58 (t, J = 2.4 Hz, 2H), 2.25-2.19 (m, 2H), 1.57-1.36 (m, 4H), 0.86 (t, J = 4.2 Hz, 3H); 13 C NMR (75 MHz CDCl 3 ) δ 137.6, 128.4, 127.8, 126.3, 82.6, 77.4, 31.1, 25.1, 22.0, 18.5, 13.6; IR (neat, cm -1 ); 2958 (w), 1606(s), 1494 (w), 1454 (m), 725 (s), 695 (s); HRMS calcd for C 13 H 16 172.1252, found:172.1255. 1-Phenyl-3-(o-methylphenyl)propyne (5a) (a mixture): 3 1 H NMR (300 MHz, CDCl 3 ) δ 7.46-7.12(m, 8H), 3.77-3.72(d, 2H), 2.35-2.32 (t, CH 3H); 13 3 C NMR (75 MHz CDCl 3 ) δ 136.1, 135.9, 134.9, 133.6, 131.9, 131.6, 131.6, 130.1, 130.0, 129.6, 129.5, 129.3, 129.2, 129.0, 128.8, 128.7, 128.6, 128.4, 128.3, 128.2, 127.8, 127.7, 127.3, 126.8, 126.2, 125.0, 123.7, 87.8, 87.2, 82.7, 82.4, 25.6, 25.3, 23.9, 21.4, 19.3. S5
1-Phenyl-3-(2,4-dimethylphenyl)propyne (5b): 1 H NMR (300 MHz, CDCl 3 ) δ 7.45-7.42 (m, 2H), 7.29-7.25 (m, 4H), 7.06-6.97 (m, 2H), 3.69 (s, 2H), 2.31 (s, 6H); 13 C NMR (75 MHz CDCl 3 ) δ 135.6, 134.7, 132.8, 131.6, 130.0, 129.1, 128.2, 127.7, 127.5, 123.8, 87.4, 82.6, 23.8, 21.0, 18.8; IR (neat, cm -1 ) 2921 (w), 1598 (w), 1501 (w), 1442 (w); HRMS calcd for C 17 H 16 220.1252, found: 220.1257. 220.1248. 1-Phenyl-3-(3,4 -dimethylphenyl)propyne (5c) (a mixture): 1 H NMR (300 MHz, CDCl 3 ) δ 7.61-7.22(m, 8H), 3.89(s, 2H), 2.44-2.37(m, 6H); 13 C NMR (75MHz CDCl 3 ) δ 136.8, 136.6, 134.9, 134.7, 134.1, 131.6, 131.5, 129.7, 129.2, 128.6, 128.1, 127.6, 126.3, 125.6, 125.3, 123.8, 88.0, 87.7, 82.6, 82.3, 25.2, 24.6, 20.5, 19.7, 19.3, 15.0; IR (neat, cm -1 ) 2931(w), 1601(w), 1507(w), 1442(w); HRMS calcd for C 17 H 16 220.1252, found: Cl 226.0549, found: 226.0551 1-Phenyl-3-(p-chlorophenyl)propyne (5d) (a mixture): 1 H NMR (300 MHz, CDCl 3 ) δ 7.47-7.27(m, 10H), 3.89 (s, 0.5H), 3.76 (s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 135.2, 134.4, 132.4, 131.6, 131.6, 129.5, 129.1, 128.6, 128.2, 128.0, 127.9, 126.9, 126.8, 123.4, 86.8, 86.1, 83.5, 83.0, 25.1, 23.9. IR (neat, cm -1 ); 2962 (w), 1599 (w), 1489 (s); HRMS calcd for C 15 H 11 Cl 1-Phenyl-3-(2, 2, 4 -trimethylphenyl)propyne (5e): 1 H NMR (300 MHz, CDCl 3 ) δ 7.35-7.33 (m, 2H), 7.23-7.21 (m, 3H), 6.86 (s, 2H), 3.66 (s, 2H), 2.40 (s, 6H), 2.25 (s, 3H); 13 C NMR (75MHz CDCl 3 ) δ 136.3, 136.1, 131.6, 131.0, 128.9, 128.0, 127.5, 123.9, 87.4, 80.1, 20.8, 19.9, 19.6; IR (neat, cm -1 ) 2918(w), 1598(w), 1489(w), 1442(w); HRMS calcd for C 18 H 18 234.1402, found: 234.1411. 1-Phenyl-3-(2, 4, 6 -triisopropylphenyl)propyne (5f): 1 H NMR (300 MHz, CDCl 3 ) δ 7.36-7.33 (m, 2H), 7.25-7.21 (m, 3H), 7.04 (s, 2H), 3.79 (s, 2H), 3.39 (hp, J = 6.9 Hz, 2H), 2.89 (h, J = 6.9 Hz, 1H), 1.32-1.25 (m, 18H); 13 C NMR (75 MHz CDCl 3 ) δ 147.3, 146.7, 131.5, 128.8, 128.1, 127.5, 124.0, 121.2, 89.0, 80.7, 34.2, 29.8, 24.1, 24.0, 18.2; IR (neat, cm -1 ) 2961(s), 1606 (w), 1469 (m); HRMS calcd for C 24 H 30 318.2348, found: 318.2343. 198.0504. S 1-Phenyl-3-(2-thienyl)propyne (5g) (a mixture): 1 H NMR (300 MHz, CDCl 3 ) δ 7.47-6.93(m, 11H), 3.98 (s, 2H), 3.79(s, 1H); 13 C NMR (75 MHz CDCl 3 ) δ 139.5, 136.9, 131.6, 130.9, 128.2, 127.9, 127.8, 127.6, 126.8, 125.0, 124.1, 123.5, 123.3, 121.3, 87.3, 86.7, 82.3, 82.0, 20.9, 20.6; IR (neat, cm -1 ) 1597 (w), 1490 (m); HRMS calcd for C 13 H 10 S 198.0503, found: S6
O 1-Phenyl-3-(2-furyl)propyne (5h) (a mixture): 1 H NMR (300 MHz, CDCl 3 ) δ 7.47-7.25 (m, 6H), 6.35-6.27 (m, 2H), 3.82 (s, 2H), 3.59 (s, 0.2H); 13 C NMR (75 MHz CDCl 3 ) δ 150.3, 141.7, 131.7, 128.2, 128.0, 123.3, 110.4, 106.2, 84.5, 81.8, 19.4; IR (neat, cm -1 ) 2921(w), 1598 (w), 1490 (m); HRMS calcd for C 13 H 10 O 182.0732, found: 182.0734. H Ph Ph H 1,3-Diphenylpropa-1,2-diene (13): 4 1 H NMR (300 MHz, CDCl 3 ) δ 7.37-7.19 (m, 10H), 6.59 (s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 207.7, 133.5, 128.8, 127.3, 127.0, 98.4. Reference (1) (a) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118. (b) Banerjee, M.; Roy, S. Org. Lett. 2004, 6, 2137-2140. (2) Hashmi, A.S.; Rudolph, M.; Schymura, S.; Visus, J.; Frey, W. Eur. J. Org. Chem. 2006. 4905-4909. (3) Ma, S.; He, Q.; Zhang, X. J. Org. Chem. 2005, 70, 3336-3338. (4) Ohno, H.; Miyamura, K.; Tanaka, T. J. Org. Chem. 2002. 67. 1359-1367. S7
Spectral for 3-Phenylprop-2-yn-1-yl trichloroacetimidates 3-Phenylprop-2-ynyl trichloroacetimidate (2a) S8
3-p-Tolylprop-2-ynyl trichloroacetimidate (2b) S9
3-o-Tolylprop-2-ynyl trichloroacetimidate (2c) S10
3-(p-Methoxyphenyl)prop-2-ynyl trichloroacetimidate (2d) S11
3-(p-Nitrophenyl)prop-2-ynyl trichloroacetimidate (2e) S12
3-(p-Bromophenyl)prop-2-ynyl trichloroacetimidate (2f) S13
Methyl 2-(3-trichloroacetimidoxyprop-1-ynyl) benzoate (2g) S14
3-(3-Formylphenyl)prop-2-ynyl trichloroacetimidate (2h) S15
3-(1-Naphthyl)prop-2-ynyl trichloroacetimidate (2i) S16
3-(5-Formylthiophen-2-yl)prop-2-ynyl trichloroacetimidate (2j) S17
Hept-2-ynyl trichloroacetimidate (2k) S18
4,4-Dimethyl-1-phenylpent-1-yn-3-yl trichloroacetimidate (6) S19
2,2,2-Trichloro-N-(1,3-diphenylprop-2-ynyl)acetamide (11) S20
1-Phenylprop-2-ynyl trichloroacetimidate (12) S21
Spectra for 1,3-diphenylprop-1-ynes 1,3-Diphenylprop-1-yne (3a) S22
1-(3-p-Tolylprop-2-ynyl)benzene (3b) S23
1-(3-o-Tolylprop-2-ynyl)benzene (3c) S24
1-(3-(p-Nitrophenyl)prop-2-ynyl)benzene (3e) S25
1-(3-(p-Bromophenyl)prop-2-ynyl)benzene (3f) S26
Methyl 2-(3-phenylprop-1-ynyl)benzoate (3g) S27
3-(3-Phenylprop-1-ynyl)benzaldehyde (3h) S28
1-(3-Phenylprop-1-ynyl)naphthalene (3i) S29
5-(3-Phenylprop-1-ynyl)thiophene-2-carbaldehyde (3j) S30
1-(Hept-2-ynyl)benzene (3k) S31
1-Phenyl-3-(o-methylphenyl)propyne (5a) (a mixture) Mixture Mixture S32
1-Phenyl-3-(2,4-dimethylphenyl)propyne (5b) S33
1-Phenyl-3-(3, 4 -dimethylphenyl)propyne (5c) (a mixture) Mixture Mixture S34
1-Phenyl-3-(p-chlorophenyl)propyne (5d) (a mixture) Mixture Mixture S35
1-Phenyl-3-(2, 2, 4 -trimethylphenyl)propyne (5e) S36
1-Phenyl-3-(2, 4, 6 -triisopropylphenyl)propyne (5f) S37
1-Phenyl-3-(2-thienyl)propyne (5g) (a mixture) Mixture Mixture S38
1-Phenyl-3-(2-furyl)propyne (5h) (a mixture) Mixture Mixture S39
1,3-Diphenylpropa-1,2-diene (13) S40