Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes
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1 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 , China R Ο NH CCl 3 + Ar-H BF 3 OEt 2 (30 mol %) rt, 5 min % R Ar Contents 1) General S2 2) Spectral data for 3-phenylprop-2-yn-1-yl trichloroacetimidates 2b-k, 6, 11, S2 3) Spectra data for 1,3-diphenylprop-1-ynes 3c-k, 5a-h, 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
2 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, 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 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 , found: 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), (m, 1H), (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 , found: 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 , found: O 2 N NH Ο CCl 3 3-(p-Nitrophenyl)prop-2-ynyl trichloroacetimidate (2e): 90 %; white solid; m.p 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 , found: S2
3 Br NH Ο CCl 3 3-(p-Bromophenyl)prop-2-ynyl trichloroacetimidate (2f): 98 %; white solid; m.p 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 , found: COOMe 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), (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 , found: 3-(3-Formylphenyl)prop-2-ynyl trichloroacetimidate (2h): 82 %; NH white solid; m.p o C; 1 H NMR (300 MHz, CDCl 3 ) δ (s, Ο Ο CCl 1H), 8.58 (s, 1H), (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 , found: NH Ο CCl 3 3-(Naphthalen-1-yl)prop-2-ynyl trichloroacetimidate (2i): 97 %; yellow solid; m.p o C; 1 H NMR (300 MHz, CDCl 3 ) δ 8.58 (s, 1H), (m, 1H), (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 , found: NH O S Ο CCl 3 H , found: (5-Formylthiophen-2-yl)prop-2-ynyl trichloroacetimidate (2j): 96 %; white solid; m.p 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), (m, 2H), (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
4 1289 (s), 1072 (s); HRMS calcd for C 9 H 12 NOCl , found: 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), (m, 2H), (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 , found: O HN CCl 3 2,2,2-Trichloro-N-(1,3-diphenylprop-2-ynyl)acetamide (11): 1 H NMR (300 MHz, CDCl 3 ) δ (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 , found: NH O CCl 3 1-Phenylprop-2-ynyl trichloroacetimidate (12): 2 61 %; white solid; m.p o C; 1 H NMR (300 MHz, CDCl 3 ) δ 8.60 (s, 1H), (m, 2H), (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, Spectra data for 1,3-diphenylprop-1-ynes 3c-k, 5a-h, (3-o-Tolylprop-2-ynyl)benzene (3c): 1 H NMR (300 MHz, CDCl 3 ) δ (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 , found: O 2 N 1-(3-(p-Nitrophenyl)prop-2-ynyl)benzene (3e): yellow solid; m.p o C; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (m, 2H), (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 , found: Br 1-(p-Bromophenyl)-3-phenylpropyne (3f) 1 H NMR (300 MHz, CDCl 3 ) δ (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 , found: S4
5 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), (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) + ] , found: H O 3-(3-Phenylprop-1-ynyl)benzaldehyde (3h): 1 H NMR (300 MHz, CDCl 3 ) δ 9.96 (s, 1H), (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 , found: (3-Phenylprop-1-ynyl)naphthalene (3i): 1 H NMR (300 MHz, CDCl 3 ) δ 8.38 (d, J = 8.1 Hz, 1H), (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 , found: 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), (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 , found: (Hept-2-ynyl)benzene (3k): 1 H NMR (300 MHz, CDCl 3 ) δ (m, 5H), 3.58 (t, J = 2.4 Hz, 2H), (m, 2H), (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 , found: Phenyl-3-(o-methylphenyl)propyne (5a) (a mixture): 3 1 H NMR (300 MHz, CDCl 3 ) δ (m, 8H), (d, 2H), (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, S5
6 1-Phenyl-3-(2,4-dimethylphenyl)propyne (5b): 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (m, 4H), (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 , found: Phenyl-3-(3,4 -dimethylphenyl)propyne (5c) (a mixture): 1 H NMR (300 MHz, CDCl 3 ) δ (m, 8H), 3.89(s, 2H), (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 , found: Cl , found: Phenyl-3-(p-chlorophenyl)propyne (5d) (a mixture): 1 H NMR (300 MHz, CDCl 3 ) δ (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, 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 (m, 2H), (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 , found: Phenyl-3-(2, 4, 6 -triisopropylphenyl)propyne (5f): 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (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), (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 , found: S 1-Phenyl-3-(2-thienyl)propyne (5g) (a mixture): 1 H NMR (300 MHz, CDCl 3 ) δ (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 , found: S6
7 O 1-Phenyl-3-(2-furyl)propyne (5h) (a mixture): 1 H NMR (300 MHz, CDCl 3 ) δ (m, 6H), (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 , found: H Ph Ph H 1,3-Diphenylpropa-1,2-diene (13): 4 1 H NMR (300 MHz, CDCl 3 ) δ (m, 10H), 6.59 (s, 2H); 13 C NMR (75 MHz CDCl 3 ) δ 207.7, 133.5, 128.8, 127.3, 127.0, Reference (1) (a) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, (b) Banerjee, M.; Roy, S. Org. Lett. 2004, 6, (2) Hashmi, A.S.; Rudolph, M.; Schymura, S.; Visus, J.; Frey, W. Eur. J. Org. Chem (3) Ma, S.; He, Q.; Zhang, X. J. Org. Chem. 2005, 70, (4) Ohno, H.; Miyamura, K.; Tanaka, T. J. Org. Chem S7
8 Spectral for 3-Phenylprop-2-yn-1-yl trichloroacetimidates 3-Phenylprop-2-ynyl trichloroacetimidate (2a) S8
9 3-p-Tolylprop-2-ynyl trichloroacetimidate (2b) S9
10 3-o-Tolylprop-2-ynyl trichloroacetimidate (2c) S10
11 3-(p-Methoxyphenyl)prop-2-ynyl trichloroacetimidate (2d) S11
12 3-(p-Nitrophenyl)prop-2-ynyl trichloroacetimidate (2e) S12
13 3-(p-Bromophenyl)prop-2-ynyl trichloroacetimidate (2f) S13
14 Methyl 2-(3-trichloroacetimidoxyprop-1-ynyl) benzoate (2g) S14
15 3-(3-Formylphenyl)prop-2-ynyl trichloroacetimidate (2h) S15
16 3-(1-Naphthyl)prop-2-ynyl trichloroacetimidate (2i) S16
17 3-(5-Formylthiophen-2-yl)prop-2-ynyl trichloroacetimidate (2j) S17
18 Hept-2-ynyl trichloroacetimidate (2k) S18
19 4,4-Dimethyl-1-phenylpent-1-yn-3-yl trichloroacetimidate (6) S19
20 2,2,2-Trichloro-N-(1,3-diphenylprop-2-ynyl)acetamide (11) S20
21 1-Phenylprop-2-ynyl trichloroacetimidate (12) S21
22 Spectra for 1,3-diphenylprop-1-ynes 1,3-Diphenylprop-1-yne (3a) S22
23 1-(3-p-Tolylprop-2-ynyl)benzene (3b) S23
24 1-(3-o-Tolylprop-2-ynyl)benzene (3c) S24
25 1-(3-(p-Nitrophenyl)prop-2-ynyl)benzene (3e) S25
26 1-(3-(p-Bromophenyl)prop-2-ynyl)benzene (3f) S26
27 Methyl 2-(3-phenylprop-1-ynyl)benzoate (3g) S27
28 3-(3-Phenylprop-1-ynyl)benzaldehyde (3h) S28
29 1-(3-Phenylprop-1-ynyl)naphthalene (3i) S29
30 5-(3-Phenylprop-1-ynyl)thiophene-2-carbaldehyde (3j) S30
31 1-(Hept-2-ynyl)benzene (3k) S31
32 1-Phenyl-3-(o-methylphenyl)propyne (5a) (a mixture) Mixture Mixture S32
33 1-Phenyl-3-(2,4-dimethylphenyl)propyne (5b) S33
34 1-Phenyl-3-(3, 4 -dimethylphenyl)propyne (5c) (a mixture) Mixture Mixture S34
35 1-Phenyl-3-(p-chlorophenyl)propyne (5d) (a mixture) Mixture Mixture S35
36 1-Phenyl-3-(2, 2, 4 -trimethylphenyl)propyne (5e) S36
37 1-Phenyl-3-(2, 4, 6 -triisopropylphenyl)propyne (5f) S37
38 1-Phenyl-3-(2-thienyl)propyne (5g) (a mixture) Mixture Mixture S38
39 1-Phenyl-3-(2-furyl)propyne (5h) (a mixture) Mixture Mixture S39
40 1,3-Diphenylpropa-1,2-diene (13) S40
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