Diradical reaction mechanisms in [3 + 2]- cycloadditions of hetaryl thioketones with alkyl- or trimethylsilyl-substituted diazomethanes
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- Dwight Dennis
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1 upporting Information for Diradical reaction mechanisms in [3 + 2]- cycloadditions of hetaryl thioketones with alkyl- or trimethylsilyl-substituted diazomethanes Grzegorz Mlostoń *1, Paulina Pipiak 1 and Heinz Heimgartner 2 Address: 1 Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, PL Łódź, Poland and 2 Department of Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, witzerland Grzegorz Mlostoń - gmloston@uni.lodz.pl *Corresponding author Experimental data for compounds 8, 9, 10 and the original 1 H and 13 C NMR spectra 1. Experimental data for compound 8, 9 and 10. CH 3 CH 3 9-Isopropylidenefluorene (9b) [1]: Yield: 85 mg (41%). White crystals; m.p C (chromatographic purification; lit. m.p. 114 C [1]). 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 4 H arom ), (m, 4 H arom ), 2.58 (s, 2 CH 3 ) ppm. C 16 H 14 (206.28): calcd. C H 6.84; found C H
2 H 3 C H 3 C 2,2 -Dimethyldispiro[9H-fluorene-9,4 -(1,3)dithiolane-5 9 -[9H]fluorene] (10b): Yield: 27 mg (12%). White crystals; m.p C (MeOH/CHCl 3 ). IR (KBr): = 2918 (w), 1445 (m), 1279 (w), 1149 (m), 1108 (w), 1033 (w), 760 (m), 744 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = 7.97 (br. s, 4 H arom ), 7.42 (t, J = 7.8Hz, 4 H arom ), 7.25 (t, J = 7.2Hz, 4 H arom ), 7.12 (t, J = 7.2Hz, 4 H arom ), 2.37 (s, 2 CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = (for 8 C arom ), 128.5, 127.8, 126.3, (for 16 CH arom ), 59.4 (C-2), 78.4 (C-4, C-5), 35.2 (2 CH 3 ) ppm. C 29 H 22 2 (434.61): calcd. C 80.14, 5.10, 14.76; found C 80.0, 5.27, CH 3 CH 3 2,2-Dimethyl-3,3-di(thiophen-2-yl)thiirane (8d): Yield: 190 mg (75%). Yellow crystals; m.p C (chromatographic purification). IR (KBr): = 3099 (w), 2955 (w), 2917 (w), 1429 (m), 1367 (m), 1244 (m), 1231 (m), 1085 (m), 1077 (m), 849 (m), 833 (s), 783 (m), 705 (s), 560 (m) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = 7.07 (dd, J = 1.2 Hz, J = 4.8 Hz, 2 H arom ), 7.00 (dd, J = 1.2 Hz, J = 3.6 Hz, 2 H arom ), (m, 2 H arom ), 1.64 (s, 2 CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = (for 2 C arom ), 127.4, 126.5, (for 6 CH arom ), 56.0, 54.8 (C-2, C-3), 26.7 (2 CH 3 ) ppm. M (EI): m/z (%) = 253 (100, [M+H] + ). C 12 H 12 3 (252.42): calcd. C 57.10, H 4.79, 38.11; found C 56.91, H 4.80, H 3 C H 3 C 2
3 2,2-Dimethyl-4,4,5,5-tetra(thiophen-2-yl)-1,3-dithiolane (10d): Yield: 74 mg (32%). White crystals; m.p C (MeOH/CHCl 3 ). IR (KBr): = 3101 (w), 3085 (w), 2916 (w), 1423 (m), 1234 (m), 1226 (m), 1156 (m), 1106 (m), 1048 (m), 856 (m), 758 (m), 707 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = 7.24 (dd, J = 1.2 Hz, J = 5.4 Hz, 4 H arom ), 7.05 (dd, J = 1.2 Hz, J = 3.6 Hz, 4 H arom ), (m, 4 H arom ),1.76 (s, 2 CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = (for 4 C arom ), 130.3, 126.3, (for 12 CH arom ), 76.1 (C-4, C-5), 57.5 (C-2), 33.1 (2 CH 3 ) ppm. M (EI): m/z (%) = 485 (100, [M+Na] + ). C 21 H 18 6 (462.76): calcd. C 54.50, H 3.92, 41.57; found C 54.44, H 3.76, e CH 3 CH 3 e 1,1-Di(selenophen-2-yl)-2-methylpropene (9e): Yield: 192 mg (61%) After desulfurization of tiirane 8d. Colorles oil that crystallized in the refrigerator. IR (film): = 3054 (m), 2926 (m), 2905 (m), 2850 (w), 1448 (m), 1368 (w), 1267 (w), 1225 (m), 1168 (w), 1078 (w), 1000 (w), 829 (w), 783 (w), 681 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = 7.98 (d, J = 6.0 Hz, 2 H arom ), (m, 2 H arom ), 7.05 (d, J = 3.6 Hz, 2 H arom ), 1.98 (s, 2 CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 151.8, (C arom, C arom -C=),), 130.7, 129.0, (for 6 CH arom ), (C=C(CH 3 ) 2 ) 23.5 (2 CH 3 ) ppm. M (EI): m/z (%) = 315 (100, [M+H] + ). C 12 H 12 e 2 (314.14): calcd. C 45.88, H 3.85; found C 46.14, H e H 3 C e H 3 C e e 2,2-Dimethyl-4,4,5,5-tetra(selenophen-2-yl)-1,3-dithiolane (10e): Yield: 56 mg (17%). White crystals; m.p C (MeOH/CHCl 3 ). IR (KBr): = 2952 (w), 2917 (w), 1434 (m), 1362 (w), 1230 (s), 1154 (m), 1103 (m), 1025 (m), 797 (m), 688 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = 7.96 (dd, J = 1.2 Hz, J = 6.0 Hz, 4 H arom ), 7.39 (dd, J = 1.2 Hz, J = 4.2 Hz, 4 H arom ), (m, 4 H arom ), 1.77 (s, 2 CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = (for 4 C arom ), 133.3, 133.2, (for 12 CH arom ),
4 (C-4, C-5), 58.1 (C-2), 33.2 (2 CH 3 ) ppm. C 21 H 18 2 e 4 (650.34): calcd. C 38.78, H 2.79, 9.86; found C 38.56, H 2.93, CH 3 CH 3 2,2-Dimethyl-3-phenyl-3-(thiophen-2-yl)thiirane (8f): Yield: 42 mg (17%). White crystals; m.p C (chromatographic purification). IR (KBr): = 2997 (w), 2919 (w), 1491 (w), 1443 (m), 1369 (w), 1228 (m), 1075 (m), 753 (m), 702 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 2 H arom ), (m, 2 H arom ), (m, 1 H arom ), 7.14 (dd, J = 1.2 Hz, J = 5.4 Hz, 1 H arom ), 7.02 (dd, J = 1.2 Hz, J = 3.6 Hz, 1 H arom ), 6.87 (dd, J = 3.6 Hz, J = 4.8 Hz, 1 H arom ), 1.68 (s, CH 3 ), 1.53 (s, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 147.3, (2 C arom ), 129.5, 127.9, 127.3, 127.2, 126.5, (for 8 CH arom ), 61.5, 54.4, (C-2, C-3), 26.3 (CH 3 ), 28.3 (CH 3 ) ppm. M (EI): m/z (%) = 247 (100, [M+H] + ). C 14 H 14 2 (246.39): calcd. C 68.25, H 5.73, 26.03; found C 68.37, H 5.56, CH 3 CH 3 1-Phenyl-1-(thiophen-2-yl)-2-methylpropene (9f) [2]: Yield 15 mg (7%). Pale yellow oil (lit. [2]: colorless liquid). 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 6 H arom ), (m, 1 H arom ), (m, 1 H arom ), 2.06 (s, CH 3 ), 1.79 (s, CH 3 ) ppm. CH 3 CH 3 e 1-Phenyl-1-(selenophen-2-yl)-2-methylpropene (9c): Yield 148 mg (57%) After desulfurization of tiirane 8f. Yellow oil. IR (film): = 3055 (m), 2907 (m), 2853 (m), 1598 (w), 1491 (m), 1442 (s), 1369 (m), 1218 (m), 1019 (m), 757 (m), 700 (s), 685 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = 7.91 (dd, J = 1.2 Hz, J = 6.0 Hz, 1 H arom ), (m, 6 H arom ), 6.97 (dd, J = 1.2 Hz, J = 3.6 Hz, 1 H arom ), 2.06 (s, CH 3 ), 1.77 (s, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 151.9, 143.7, 132.7, (2 C arom, 4
5 C arom -C=C(CH 3 ) 2 ), 130.3, 129.4, 129.0, 128.6, 128.0, (for 8 CH arom ), 23.5 (CH 3 ), 22.8 (CH 3 ) ppm. M (EI): m/z (%) = 263 (100, [M+2H] + ), 261 (40, [M] + ). C 14 H 14 e (261.22): calcd. C 64.37, H 5.40; found C 64.41, H H 3 C H 3 C e e 2,2-Dimethyl-4,5-diphenyl-4,5-di(selenophen-2-yl)-1,3-dithiolane (10c): Isolated as a mixture of cis,trans-isomers (crude product ratio 72 : 28). Yield: 30 mg (11%). White crystals; m.p C (MeOH/CHCl 3 ). IR (KBr): = 3057 (w), 2922 (w), 2853 (w), 1596 (w), 1490 (m), 1444 (s), 1364 (m), 1232 (m), 1181 (m), 1155 (m), 1033 (m), 931 (m), 692 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 32 H arom ), 1.87 (s, CH 3 cis), 1.74 (s, 2 CH 3 trans), 1.36 (s, CH 3 cis) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = br., br. (for 8 C arom ), 133.1, 132.9, 132.8, 131.6, 131.2, 130.8, 128.0, 127.9, 127.6, 127.1, 127.0, (for 32 CH arom ), 80.5, 80.0 (C-4 + C- 5, for cis and trans), 55.6, 55.3 (C-2, cis and trans), 33.2 (2 CH 3 trans), 33.0 (CH 3 cis), 32.7 (CH 3 cis) ppm. C 25 H 22 2 e 2 (544.49): calcd. C 55.15, H 4.07, 11.78; found C 55.32, H 4.26, CH 3 O CH 3 1-Phenyl-1-(furan-2-yl)-2-methylpropene (9g) [2b]: Yield 79 mg (40%) After desulfurization of tiirane 8g. Pale yellow oil (lit. [2b]: a liquid isolated by distillation under reduced pressure). 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 4 H arom ), (m, 2 H arom ), (m, 1 H arom ), 5.96 (d, J = 3.0 Hz, 1 H arom ), 2.17 (s, CH 3 ), 1.75 (s, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 155.5, 141.2, 133.3, (2 C arom, C arom C=C(CH 3 ) 2 ), 140.9, 129.9, 128.0, 126.6, 110.4, (for 8 CH arom ), 23.3 (CH 3 ), 22.4 (CH 3 ) ppm. 5
6 H 3 C H 3 C O O 2,2-Dimethyl-4,5-diphenyl-4,5-di(furan-2-yl)-1,3-dithiolane (10g): Isolated as a mixture of cis,trans-isomers (crude product ratio 58:42). Yield: 59 mg (28%). White crystals; m.p C (MeOH/CHCl 3 ). IR (KBr): = 3110 (w), 3058 (w), 2921 (m), 2855 (w), 1598 (w), 1490 (s), 1445 (s), 1149 (s), 1037 (m), 1017 (s), 932 (m), 795 (m), 750 (s), 718 (s), 696 (s), 595 (m) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 32 CH arom ) 1.99 (s, CH 3 cis), 1.72 (s, 2 CH 3 trans), 1.53 (s, CH 3 cis) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 155.0, 154.9, 140.0, (for 8 C arom ), 141.0, 140.6, 130.5, 129.8, 127.6, 127.3, 127.2, 126.5, 112.9, 110.9, 110.3, (for 32 CH arom ), 76.1, 76.0 (C-4 + C-5, for cis and trans), 55.8, 54.9 (C-2, cis and trans), 34.8 (CH 3 cis), 33.7 (2 CH 3 trans), 32.3 (CH 3 cis) ppm. C 25 H 22 O 2 2 (418.57): calcd. C 71.74, H 5.30, 15.32; found C 71.87, H 5.28, e CH 3 CH 3 Cl 1-(4-Chlorophenyl)-1-(selenophen-2-yl)-2-methylpropene (9h): Yield: 168 mg (65%) After desulfurization of tiirane 8h. Yellow oil. IR (film): = 3056 (w), 2908 (m), 2852 (m), 1901 (w), 1590 (w), 1488 (s), 1448 (m), 1229 (m), 1218 (m), 1091 (s), 1014 (s), 855 (m), 833 (m), 817 (s), 776 (s), 685 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 1 H arom ), (m, 5 H arom ), (m, 1 H arom ), 2.05 (s, CH 3 ), 1.77 (s, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 151.3, 142.0, 133.5, 132.4, (3 C arom, C arom C=C(CH 3 ) 2 ), 130.9, 130.6, 129.1, 128.9, (for 7 CH arom ), 22.8 (CH 3 ), 22.3 (CH 3 ) ppm. C 14 H 13 Cle (259.67): calcd. C 56.87, H 4.43; found C 56.96, H
7 Cl H 3 C H 3 C e e Cl 2,2-Dimethyl-4,5-di(4-chlorophenyl)-4,5-di(selenophen-2-yl)-1,3-dithiolane (10h): Isolated as a mixture of cis,trans-isomers (crude product ratio 70:30). Yield: 53 mg (17%). White crystals; m.p C (MeOH/CHCl 3 ). IR (KBr): = 2919 (w), 2851 (w), 1587 (w), 1489 (s), 1230 (m), 1095 (s), 1012 (s), 785 (m), 688 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 28 H arom ), 1.85 (s, CH 3 cis), 1.72 (s, 2 CH 3 trans), 1.44 (s, CH 3 cis) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 157.3, 156.6, 142.6, (for 8 C arom ), 133.6, 133.2, 133.1, 132.9, 132.8, 132.5, 132.3, 132.1, 128.0, 127.1, (for 32 CH arom ), 79.7, 79.4 (C-4 + C-5, for cis and trans), 56.0, 55.9 (C-2, cis and trans), 33.1 (CH 3 cis), 33.0 (2 CH 3 trans), 32.7 (CH 3 cis) ppm. C 25 H 20 Cl 2 2 e 2 (613.38): calcd. C 48.95, H 3.29, 10.45; found C 48.73, H 3.50, CH 3 H 9-Ethylidenefluorene (9j) [3]: Yield: 6 mg (6%). Pale yellow crystals; m.p C (isolated by PLC). (Lit. [3a], m.p ); lit. [3b], m. p C). 1 H NMR (600 MHz, CDCl 3 ): δ = 7.92 (d, J = 7.2 Hz, 1 H arom ), 7.79 (d, J = 7.2 Hz, 1 H arom ), 7.73 (d, J = 7.2 Hz, 1 H arom ), 7.68 (d, J = 7.2 Hz, 1 H arom ), (m, 4 H arom ), 6.89 (q, J = 7.2 Hz, =CH), 2.43 (d, J = 7.2 Hz, CH 3 ) ppm. 7
8 H 3 C H 2 -Methyldispiro[9H-fluorene-9,4 -(1,3)dithiolane-5 9 -[9H]fluorene] (10j): Yield: 65 mg (61%). White crystals; m.p C (MeOH/CHCl 3 ). IR (KBr): = 3052 (w), 3028 (w), 1474 (w), 1445 (m), 1279 (w), 1157 (w), 1033 (w), 739 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 8 H arom ), (m, 4 H arom ), 7.00 (s br., 4 H arom ), 5.51 (q, J = 6.0 Hz, =CH) 2.00 (d, J = 6.0 Hz, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 140.2, (for 8 C arom ), 128.5, 128.4, 127.2, 126.6, 126.5, 126.4, 119.4, (for 16 CH arom ), 76.1 (C-4, C-5), 46.8 (C-2), 22.2 (CH 3 ) ppm. C 28 H 20 2 (420.59): calcd. C 79.96, 4.79, 15.25; found C 79.73, H 4.77, H 3 C H 2-Methyl-4,4,5,5-tetra(thiophen-2-yl)-1,3-dithiolane (10k): Yield: 160 mg (72%). Yellow crystals; m.p C (MeOH/CHCl 3 ). IR (KBr): = 3097 (w), 3070 (w), 2918 (w), 1424 (m), 1227 (s), 1187 (w), 1045 (m), 856 (m), 753 (m), 703 (s) cm H NMR (600 MHz, CDCl 3 ): δ = (m, 4 H arom ), (m, 2 H arom ), (m, 2 H arom ), (m, 4 H arom ), 4.77 (q, J = 6.6 Hz, CH(CH 3 )), 1.79 (d, J = 6.6 Hz, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 146.2, (for 4 C arom ), 130.3, 129.4, 126.9, 126.1, 125.8, (for 12 CH arom ), 74.8 (C-4, C-5), 45.0 (C-2), 18.9 (CH 3 ) ppm. C 20 H 16 6 (448.73): calcd. C 53.53, H 3.59, 42.87; found C 53.62, H 3.83, e CH 3 e H 8
9 1,1-Di(selenophen-2-yl)propene (9l): Yield: 10 mg (3 %). Pale yellow oil. IR (film): = 3055 (w), 2926 (w), 1724 (w), 1444 (m), 1246 (m), 1221 (m), 1022 (w), 841 (w), 816 (m), 793 (w), 742 (w), 684 (s) cm H NMR (600 MHz, CDCl 3 ): δ = (m, 1 H arom ), (m, 1 H arom ), (m, 1 H arom ), (m, 2 H arom ), (m, 1 H arom ), 6.24 (q, J = 7.2 Hz, =CH), 1.82 (d, J = 7.2 Hz, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 153.3, 145.9, (2 C arom, C arom -C=), 131.3, 129.9, 129.8, 129.1, 128.7, 127.0, (6 CH arom, =CH), 15.9 (CH 3 ) ppm. C 11 H 10 e 2 (300.12): calcd. C 44.02, H 3.36; found C 44.00, H e H 3 C H e e e 2-Methyl-4,4,5,5-tetra(selenophen-2-yl)-1,3-dithiolane (10l): Yield: 252 mg (79%). White crystals; m.p C (MeOH/CHCl 3 ). IR (KBr): = 3088 (w), 3048 (w), 2914 (w), 1439 (m), 1375 (w), 1230 (s), 1022 (m), 829 (w), 787 (w), 682 (s) cm H NMR (600 MHz, CDCl 3 ): δ = (m, 4 H arom ), (m, 2 H arom ), (m, 2 H arom ), (m, 4 H arom ), 4.8 (q, J = 6.6 Hz, CH(CH 3 )), 1.76 (d, J = 6.6 Hz, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 154.5, (for 4 C arom ), 134.1, br., 132.3, 128.2, (for 12 CH arom ), 78.4 (C-4, C-5), 45.6 (C-2), 19.1 (CH 3 ) ppm. C 20 H 16 2 e 4 (636.31): calcd. C 37.75, H 2.53, 10.08; found C 37.67, H 2.65, CH 3 H 1-Phenyl-1-(thiophen-2-yl)propene (9m): Isolated as a mixture of (E/Z)-isomers (53:47). Yield: 96 mg (48%) After desulfurization of tiirane 8m. Yellow oil. IR (film): = 3062 (w), 2931 (w), 1716 (m), 1682 (m), 1635 (s), 1599 (m), 1578 (m), 1515 (m), 1447 (m), 1413 (s), 1354 (m), 1288 (s), 1232 (m), 1053 (m), 843 (m), 717 (s), 700 (s), 649 (m) cm H NMR (600 MHz, CDCl 3 ): δ = (m, 16 H arom ), 6.17 (q, J = 7.2 Hz, =CH), 6.02 (q, J = 7.2 Hz, =CH), 1.86 (d, J = 7.2 Hz, CH 3 ), 1.60 (d, J = 7.2 9
10 Hz, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 147.4, 143.2, 141.6, 139.1, 136.7, (4 C arom, 2 C arom -C=), 129.7, 128.2, 128.0, 127.8, 127.5, 127.3, 127.1, 126.8, 126.6, 125.4, 124.6, 123.4, (for 16 CH arom, 2 (=CH)), 16.0 (CH 3 ), 15.2 (CH 3 ). C 13 H 12 (200.30): calcd. C 77.95, H 6.04, 16.01; found C 78.0, H 5.79, H 3 C H 2-Methyl-4,5-diphenyl-4,5-di(thiophen-2-yl)-1,3-dithiolane (10m): Isolated as a mixture of two cis,trans-isomers in a ratio of 56:44 (from three isomers possible). Yield: 58 mg (27%). Yellow crystals; m.p C (MeOH/CHCl 3 ). IR (KBr): = 3055 (w), 2922 (w), 1597 (w), 1488 (s), 1443 (s), 1371 (w), 1233 (w), 1187 (m), 1052 (m), 1034 (m), 850 (w), 695 (s) cm H NMR (600 MHz, CDCl 3 ): δ = (m, 32 H arom ), 4.38 (q, J = 6.6 Hz, CH(CH 3 )), 4.09 (q, J = 6.6 Hz, CH(CH 3 )), 1.68 (d, J = 6.6 Hz, CH 3 ), 1.61 (d, J = 6.6 Hz, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 151.1, 149.8, 148.7, 143.4, 143.3, (for 8 C arom ), 131.2, 130.8, 130.6, 130.4, 130.3, 130.2, 127.7, 127.3, 127.2, 126.8, 126.7, 126.4, 126.2, 126.1, 125.5, 125.4, 125.3, (for 32 CH arom ), 77.7, 77.6, 76.4, 76.9 (2 C-4, 2 C-5), 43.3, 43.1 (2 C-2), 17.8 (CH 3 ), 18.7 (CH 3 ) ppm. C 24 H 20 4 (436.68): calcd. C 66.01, H 4.62, 29.37; found C 66.00, H 4.71, CH 3 e H 1-Phenyl-1-(selenophen-2-yl)propene (9n): Isolated as a mixture of (E/Z)-isomers (73:27). Yield: 176 mg (71%) After desulfurization of tiirane 8n. Red oil. IR (film): = 3055 (w), 3020 (w), 2928 (w), 2909 (w), 2852 (w), 1491 (m), 1441 (m), 1220 (m), 819 (m), 787 (m), 702 (s), 685 (s). 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 16 H arom ), 6.17 (q, J = 7.2 Hz, =CH), 6.09 (q, J = 7.2 Hz, =CH), 1.93 (d, J = 7.2 Hz, CH 3 ), 1.65 (d, J = 7.2 Hz, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 153.7, 147.8, 143.4, 10
11 139.2, 138.8, (4 C arom, 2 C arom C=), 131.1, 130.0, 129.9, 129.6, 129.1, 128.2, 128.1, 128.0, 127.6, 127.2, 127.1, 126.0, (for 16 CH arom, 2 =CH), 16.0 (CH 3 ), 15.4 (CH 3 ). C 13 H 12 e (247.19): calcd. C 63.16, H 4.89; fund C 62.98, H 3 C H e e 2-Methyl-4,5-diphenyl-4,5-di(selenophen-2-yl)-1,3-dithiolane (10n): Isolated as a mixture of two cis/trans-isomers in a ratio of 52:48 (from three isomers possible). Yield: 74 mg (28%). Yellow crystals: m.p C (MeOH/CHCl 3 ). IR (KBr): = 3053 (w), 2922 (w), 1596 (w), 1486 (s), 1441 (s), 1371 (m), 1232 (s), 1185 (m), 1032 (m), 685 (s) cm H NMR (600 MHz, CDCl 3 ): δ (m, 32 H arom ), 4.54 (q, J = 6.6 Hz, CH(CH 3 )), 4.12 (q, J = 6.6 Hz, CH(CH 3 )), 1.78 (d, J = 6.6 Hz, CH 3 ), 1.68 (d, J = 6.6 Hz, CH 3 ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 160.2, 157.9, 156.2, 143.7, 143.4, (for 8 C arom ), 133.2, 132.7, 132.6, 132.5, 132.4, 131.6, 131.0, 130.6, 130.3, 128.2, 128.0, 127.8, 127.6, 127.5, 127.3, 126.9, 126.8, (for 32 CH arom ), 79.3, 79.2, 78.7, 78.1 (2 C-4, 2 C-5), 43.4, 43.3 (2 C-2), 18.6 (CH 3 ), 17.7 (CH 3 ) ppm. C 24 H 20 2 e 2 (530.47): calcd. C 54.34, H 3.80, 12.09; found C 54.39, H 3.77, ,4,5,5-Tetraphenyl-2-trimethylsilyl-1,3-dithiolane (10o): Yield: 79 mg (33%). Colorless crystals: m.p C (CH 3 OH/CH 2 Cl 2 ). IR (KBr): = 3054 (w), 2952 (w), 2842 (w), 1603 (w), 1494 (m), 1437 (m), 1246 (m), 864 (s), 835 (s), 722 (s), 694 (s) cm H NMR (600 MHz, CDCl 3 ): (m, 20 H arom ), 3.36 (s, ((CH 3 ) 3 i)hc), 0.34 (s, (CH 3 ) 3 i) ppm. 13 C NMR (150 MHz, CDCl 3 ): (for 4 C arom ), br., br., 129.2, 128.1, 127.8, br., br. (for 20 CH arom ), 79.5 (C-4,C-5), 11
12 33.4 (C-2), ((CH 3 ) 3 i) ppm. HR-EI-M: (calcd for C 30 H 30 2 i [M] + ). 2,2,3,3-Tetraphenyl-5,6-bis(trimethylsilyl)-1,4-dithiane (4c) (in analogy to 4d tentatively described as a trans-isomer): Yield: 65 mg (22%). Colorless crystals: m.p C (CH 3 OH/CH 2 Cl 2 ). IR (KBr): = 3058 (w), 2941 (w), 2860 (w), 1487 (m), 1434 (m), 1250 (s), 1108 (w), 857 (s), 718 (s), 694 (s) cm H NMR (600 MHz, CDCl 3 ): (m, 4 H arom ), (m, 4 H arom ), (m, 12 H arom ), 2.97 (s, (2 (CH 3 ) 3 i)hc), 0.14 (s, 2 (CH 3 ) 3 i) ppm. 13 C NMR (150 MHz, CDCl 3 ): 146.7, (for 4 C arom ), 135.0, 132.0, 126.5, 126.2, 125.8, (for 20 CH arom ), 63.9 (C- 5, C-6), 36.3 (2 CHi), 0.17 (2 (CH 3 ) 3 i) ppm. C 34 H 40 2 e 2 (568.98): calcd. C 71.77, H 7.09, 11.27; found C 71.77, H 7.13, EI-M (MeOH): 591(100, [M+Na]. 4,4,5,5-Tetra(selenophen-2-yl)-2-trimethylsilyl-1,3-dithiolane (10s): Yield: 265 mg (76%). Yellow crystals: m.p C (hexane/ch 2 Cl 2 ). IR (KBr): = 2949 (w), 1439 (m), 1251 (s), 1225 (s), 1156 (w), 1120 (m), 1104 (w), 844 (s), 805 (m), 694 (s) cm H NMR (600 MHz, CDCl 3 ): (m, 2 H arom ), (m, 2 H arom ), (m, 2 H arom ), (m, 2 H arom ), (m, 4 H arom ), 4.02 (s, ((CH 3 ) 3 i)hc), 0.31 (s, (CH 3 ) 3 i) ppm. 13 C NMR (150 MHz, CDCl 3 ): 156.0, (for 4 arom. C), 133.8, 132.8, 132.2, 131.9, 128.3, (for 12 CH arom ), 78.2 (C-4, C-5), 37.4 (C-2), 1.46 ((CH 3 ) 3 i) ppm. C 22 H 22 2 e 4 i (694.47): calcd. C 38.05, H 3.19, 9.23; found C 38.08, H 3.21,
13 References [1] Rabinovitz, M.; Agranat, I.; Bergrnann, E. D., J. Chem. oc., 1967, doi: /J [2] a) Ganapathy, D.; ekar G.; Org. Lett. 2014, 16, , doi: /ol b) Cantrell, T..; J. Org. Chem., 1974, 3, doi: /jo00929a024. [3] a) Bell, T. W.; Catalano, V. J.; Drew, M. G. B.; Phillips, D. J.; Chem. Eur. J., 2002, 8, , doi: / b) Boyce, R.; Hayes, B. A.; Murphy, W.., J. Chem. oc. Perkin Trans. 1, 1975, doi: /P Collection of the 1 H- and 13 C-NMR for the described compounds 8, 9, and 10 Figure 1: The 1 H NMR spectrum of compound 8a. 13
14 Figure 2: The 13 C NMR spectrum of compound 8a. Figure 3: The 1 H NMR spectrum of compound 10b. 14
15 Figure 4: The 13 C NMR spectrum of compound 10b. Figure 5: The 1 H NMR spectrum of compound 8d. 15
16 Figure 6: The 13 C NMR spectrum of compound 8d. Figure 7: The 1 H NMR spectrum of compound 9d. 16
17 Figure 8: The 13 C NMR spectrum of compound 9d. 17
18 Figure 9: The 1 H NMR spectrum of compound 10d. Figure 10: The 13 C NMR spectrum of compound 10d. 18
19 Figure 11: The 1 H NMR spectrum of compound 9e. Figure 12: The 13 C NMR spectrum of compound 9e. 19
20 Figure 13: The 1 H NMR spectrum of compound 10e. Figure 14: The 13 C NMR spectrum of compound 10e. 20
21 Figure 15: The 1 H NMR spectrum of compound 8f. Figure 16: The 13 C NMR spectrum of compound 8f. 21
22 Figure 17: The 1 H NMR spectrum of compound 10f. Figure 18: The 13 C NMR spectrum of compound 10f. 22
23 Figure 19: The 1 H NMR spectrum of compound 9c. Figure 20: The 13 C NMR spectrum of compound 9c. Figure 21: The 1 H NMR spectrum of compound 10c. 23
24 Figure 22: The 13 C NMR spectrum of compound 10c. Figure 23: The 1 H NMR spectrum of compound 10g. 24
25 Figure 24: The 13 C NMR spectrum of compound 10g. Figure 25: The 1 H NMR spectrum of compound 9h. 25
26 Figure 26: The 13 C NMR spectrum of compound 9h. Figure 27: The 1 H NMR spectrum of compound 10h. 26
27 Figure 28: The 13 C NMR spectrum of compound 10h. Figure 29: The 1 H NMR spectrum of compound 10j. 27
28 Figure 30: The 13 C NMR spectrum of compound 10j. Figure 31: The 1 H NMR spectrum of compound 9k. 28
29 Figure 32: The 13 C NMR spectrum of compound 9k. Figure 33: The 1 H NMR spectrum of compound 10k. 29
30 Figure 34: The 13 C NMR spectrum of compound 10k. Figure 35: The 1 H NMR spectrum of compound 9l. 30
31 Figure 36: The 13 C NMR spectrum of compound 9l. Figure 37: The 1 H NMR spectrum of compound 10l. 31
32 Figure 38: The 13 C NMR spectrum of compound 10l. Figure 39: The 1 H NMR spectrum of compound 9m. 32
33 Figure 40: The 13 C NMR spectrum of compound 9m. Figure 41: The 1 H NMR spectrum of compound 10m. 33
34 Figure 42: The 13 C NMR spectrum of compound 10m. Figure 43: The 1 H NMR spectrum of compound 9n. 34
35 Figure 44: The 13 C NMR spectrum of compound 9n. Figure 45: The 1 H NMR spectrum of compound 10n. 35
36 Figure 46: The 13 C NMR spectrum of compound 10n. Figure 47: The 1 H NMR spectrum of compound 10o. 36
37 Figure 48: The 13 C NMR spectrum of compound 10o. Figure 49: The 1 H NMR spectrum of compound 4c. 37
38 Figure 50: The 13 C NMR spectrum of compound 4c. Figure 51: The 1 H NMR spectrum of compound 10r. 38
39 Figure 52: The 13 C NMR spectrum of compound 10r. Figure 53: The 1 H NMR spectrum of compound 10s. 39
40 Figure 54: The 13 C NMR spectrum of compound 10s. 40
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