Supporting Information. for. A novel application of 2-silylated 1,3-dithiolanes for the. synthesis of aryl/hetaryl-substituted ethenes and
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1 Supporting Information for A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes Grzegorz Mlostoń *1, Paulina Pipiak 1, Róża Hamera-Fałdyga 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, Switzerland Grzegorz Mlostoń - gmloston@uni.lodz.pl *Corresponding author Dedicated to Professor Tadeusz Marek Krygowski (Warsaw) on the occasion of his 80th birthday Experimental data for compounds 9, 13, 15 and copies of the original 1 H and 13 C NMR spectra S1
2 1. Experimental data for compounds 9, 13 and 15. 1,1,2,2-Tetraphenylethene (9a): [S1] Yield: 298 mg (90%); chromatografic purification (petroleum ether/ch 2 Cl 2 7:3). White crystals; m.p C (ref. [S1] : C). 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 12 H arom ), (m, 8 H arom ), ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = (1 signal for 4 C arom ), (1 signal for 2 C=), 131.3, 127.6, (3 signals for 20 CH arom ) ppm. 1,1,2,2-Tetrakis(thiophene-2-yl)ethene (9b): [S2] Yield: 158 mg (89%); chromatografic purification (petroleum ether/ch 2 Cl 2 8:2). Yellow crystals; m.p C (ref. [S2] : C). 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 4 H arom ), (m, 4 H arom ), (m, 4 H arom ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = (4 C arom ), (2 C=), 129.9, 127.6, 126.6, (12 CH arom ) ppm. 1,2-Bis(furan-2-yl)-1,2-bis(selenophen-2-yl)ethene (9d, mixture of E/Z isomers, ratio 1:0.7): Yield: 135 mg (65%); chromatografic purification (petroleum ether/chcl 3 8:2). Yellow crystals; m.p C. IR (KBr): = 3098 (w), 3053 (w), 1480 (m), 1429 S2
3 (m), 1251 (m), 1216 (m), 1154 (m), 1144 (m), 1074 (m), 1011 (s), 924 (m), 884 (m), 811 (m), 739 (s), 687 (s) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = 8.06 (dd, J = 5.4 Hz, 1.2 Hz, 4 H arom ), (m, 2 H arom ), (m, 2 H arom ), (m, 6 H arom ), 7.04 (dd, J = 4.2 Hz, 1.2 Hz, 2 H arom ), 6.44 (m, 2 H arom ), (m, 2 H arom ), 6.38 (d, J = 3.6 Hz, 2 H arom ), 6.17 (d, J = 3.6 Hz, 2 H arom ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 153.4, 154.2, 149.5, (8 C arom ), 125.8, (4 C=), 142.4, 142.3, 133.8, 132.9, 132.9, 132.7, 131.5, 129.2, 129.0, 113.4, 111.7, 111.6, (24 CH arom ) ppm. C 18 H 12 O 2 Se 2 (418.21): calcd. C 51.70, H 2.89; found: C 51.69, H ,2-Diphenyl-1,2-bis(thiophen-2-yl)ethene (9e, [S3] mixture of E/Z isomers, ratio 3:2): Yield: 128 mg (75%); chromatografic purification (petroleum ether/ch 2 Cl 2 8:2). Yellow crystals; m.p C. 1 H NMR (600 MHz, CDCl 3 ): δ = 7.38 (br.s, 10 H arom ), 7.25 (dd, J = 4.8 Hz, 1.2 Hz, 2 H arom ), 7.10 (br.s, 10 H arom ), 7.05 (dd, J = 4.8 Hz, 1.2 Hz, 2 H arom ), 6.88 (dd, J = 4.8 Hz, 3.6 Hz, 2 H arom ), 6.79 (dd, J = 3.6 Hz, 1.2 Hz, 2 H arom ), 6.70 (dd, J = 4.8 Hz, 3.6 Hz, 2 H arom ), 6.37 (dd, J = 3.6 Hz, 1.2 Hz, 2 H arom ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 145.9, 145.8, 142.7, 142.3, 134.7, (8 C arom, 4 C=), 131.0, 130.9, 129.7, 129.4, 128.8, 128.0, 127.6, 126.9, 126.8, 126.7, 126.5, (32 CH arom ) ppm. S3
4 9-(Diphenylmethylene)-9H-fluorene (9g): [S4] Yield: 119 mg (72%); chromatografic purification (petroleum ether/ethyl acetate 9:1). Pale yellow solid; m.p C (ref. [S4] : C). 1 H NMR (600 MHz, CDCl 3 ): δ = 7.71 (d, J = 7.8 Hz, 2 H arom ), (m, 10 H arom ), (m, 2 H arom ), (m, 2 H arom ), 6.64 (d, J = 7.8 Hz, 2 H arom ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 145.5, 143.0, 138.7, 134.2, (5 signals for 8 C arom ), 140.5, 129.6, 128.8, 128.2, 126.4, 124.9, (7 signals for 18 CH arom ) ppm. 9,9 -Bis(fluorenylidene) (9h): [S5] Yield: 115 mg (70%); chromatografic purification (petroleum ether/ethyl acetate 8:2). Orange solid; m.p C (ref. [S5] : C). 1 H NMR (600 MHz, CDCl 3 ): δ = 8.40 (d, J = 7.8 Hz, 4 H arom ), 7.72 (d, J = 7.8 Hz, 4 H arom ), (m, 4 H arom ), (m, 4 H arom ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 141.3, 141.0, (3 signals for 10 C arom ), 129.1, 126.8, 126.7, (4 signals for 16 CH arom ) ppm. 5-(9H-Fluoren-9-ylidene)-5H-dibenzo[a,d][7]annulene (tetrabenzosesquifulvalene) (9j) [S6] : Yield: 117 mg (66 %); Pale yellow solid; m.p C (ref. [S6] : C). 1 H NMR (600 MHz, CDCl 3 ): δ = 7.65 (d, J = 7.2 Hz, 2 H arom ), 7.60 (dd, J = 1.2 Hz, J= 7.2 Hz, 2 H arom ), 7.54 (dd, J = 1.2 Hz, J= 7.2 Hz, 2 H arom ), (m, 4 H arom ), 7.23 (dt, J = 0.6 Hz, J= 7.8 Hz, 2 H arom ), 7.05 (s, 2 H arom ), 6.91 (dt, J = 0.6 Hz, J=7.8 Hz, 2 H arom ), 6.47 (d, J = 7.8 Hz, 2 H arom ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = S4
5 141.2, 140.6, 138.0, 137.9, 133.6, (6 signals for 10 C arom ),130.8, 128.6, 128.4, 127.8, 127.4, 127.0, 126.4, 125.1, (9 signals for 18 CH arom ), ppm. 5-(9H-Fluoren-9-ylidene)-10,11-dihydro-5H-dibenzo[a,d][7]annulene (9k) [S7] : Yield: 220 mg (62 %); Pale yellow solid; m.p C (ref. [S7] : 296 C). 1 H NMR (600 MHz, CDCl 3 ): δ = 7.72 (d, J = 7.8 Hz, 2 H arom ), 7.44 (d, J= 7.2 Hz, 2 H arom ), (m, 6 H arom ), (m, 2 H arom ), (m, 2 H arom ), 6.88 (dd, J = 0.6 Hz, J=7.8 Hz, 2 H arom ), (m, 2 H arom ), (m, 2 H arom ) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 144.6, 141.6, 140.5, 138.2, 136.7, (6 signals for 10 C arom ), 130.1, 128.1, 127.7, 127.6, 126.4, 126.1, 125.3, (8 signals for 16 CH arom ), 31.9 (1 signal for 2 CH 2 ) ppm. 2-Methyl-2-(trimethylsilyl)-1,3-dithiolane (13a): Yield: 130 mg (68%); colorless solid, m.p C. IR (KBr): = 2949 (s), 2927 (m), 2855 (w), 1442 (m), 1369 (w), 1245 (s), 1097 (w), 1059 (w), 1006 (w), 840 (s), 755 (m), 701 (m), 620 (w) cm 1. 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), 1.61 (s, 3H), 0.17 (s, 9H) ppm. C 7 H 16 S 2 Si (192.42): calcd. C 43.69, H 8.38, S ; found: C 43.63, H 8.31, S Methyl-1,3-dithiolane (15a): Yield: 35 mg (58 %); colorless oil (ref. [S8], colorless oil, b.p. 76 C/23 Torr). 1 H NMR (600 MHz, CDCl 3 ): δ = 4.63 (q, J = 6.6 Hz, 1 H), 3.21 S5
6 3.36 (m, 4 H), 1.63 (d, J = 6.6 Hz, 3 H) ppm. 13 C NMR (150 MHz, CDCl 3 ): δ = 48.2 (CH), 39.1 (CH 2 CH 2 ), 24.7 (CH 3 ) ppm. 2-Phenyl-1,3-dithiolane (15b): Yield: 68 mg (74 %) (colorless oil, chromatographic purification: petroleum ether/ch 2 Cl 2 9:1) (ref. [S9, S10], colorless oil). 1 H NMR (600 MHz, CDCl 3 ): δ = (m, 2H), (m, 3H), 5.57 (s, 1H), (m, 4 H) ppm. References [S1] S. Rele, S. Talukdar, A. Banerji, S. Chattopadhyay, J. Org. Chem. 2001, 66, doi: /jo001586a [S2] T. Suzuki, H. Shiohara, M. Monobe, T. Sakimura, S. Tanaka, Y. Yamashita, T. Miyashi, Angew. Chem. Int. Ed. 1992, 31, doi: /anie [S3] E. Fischer, J. Larsen, J. B. Christensen, M. Fourmigué, H. G. Madsen, N. Harrit, J. Org. Chem. 1996, 61, doi: /jo960022x [S4] A. Schönberg, K.-H. Brosowski, E. Singer, Chem. Ber. 1962, 95, doi: /cber [S5] H.-J. Lubberger, E. Mueller, J. Hofmann, H. Fischer, J. C. Jochims, Chem. Ber. 1991, 124, doi: /cber [S6] L. Salisbury, J. Org. Chem. 1970, 35, doi: /jo00837a636 [S7] M. L. T. M. B. Franco, B. J. Herold, J. C. Evans, Ch. C. Rowlands, J. Chem. Soc. Perkin Trans. II 1988, doi: /p [S8] K.-D. Asmus, D. Bahnemann, Ch.-H. Fischer, D. Veltwisch, J. Am. Chem. Soc. 1979, 101, S6
7 doi: /ja00512a035 [S9] H. Tani, K. Masumoto, T. Inamasu, Tetrahedron Lett. 1991, 32, doi: /S (00) [S10] M. H. Ali, M. G. Gomes, Synthesis 2005, doi: /s Copies of 1 H and 13 C NMR spectra for compounds 9, 13, and 15 Figure S1. The 1 H NMR spectrum of compound 9a. S7
8 Figure S2. The 13 C NMR spectrum of compound 9a. Figure S3. The 1 H NMR spectrum of compound 9b. S8
9 Figure S4. The 13 C NMR spectrum of compound 9b. Figure S5. The 1 H NMR spectrum of compound 9c. S9
10 Figure S6. The 13 C NMR spectrum of compound 9c. Figure S7. The 1 H NMR spectrum of compound 9d. S10
11 Figure S8. The 13 C NMR spectrum of compound 9d. Figure S9. The 1 H NMR spectrum of compound 9e. S11
12 Figure S10. The 13 C NMR spectrum of compound 9e. Figure S11. The 1 H NMR spectrum of compound 9f. S12
13 Figure S12. The 13 C NMR spectrum of compound 9f. Figure S13. The 1 H NMR spectrum of compound 9g. S13
14 Figure S14. The 13 C NMR spectrum of compound 9g. Figure S15. The 1 H NMR spectrum of compound 9h. S14
15 Figure S16. The 13 C NMR spectrum of compound 9h. Figure S17. The 1 H NMR spectrum of compound 9i. S15
16 Figure S18. The 13 C NMR spectrum of compound 9i. Figure S19. The 1 H NMR spectrum of compound 9j. S16
17 Figure S20. The 13 C NMR spectrum of compound 9j. Figure S21. The 1 H NMR spectrum of compound 9k. S17
18 Figure S22. The 13 C NMR spectrum of compound 9k. Figure S23. The 1 H NMR spectrum of compound 13a. S18
19 Figure S24. The 1 H NMR spectrum of compound 13b. Figure S25. The 13 C NMR spectrum of compound 13b. S19
20 Figure S26. The 1 H NMR spectrum of compound 15a. Figure S27. The 13 C NMR spectrum of compound 15a. S20
21 Figure S28. The 1 H NMR spectrum of compound 15b. S21
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# School of Pharmaceutical Sciences, Zhengzhou University, 100 Kexue Avenue, Zhengzhou, Henan , China.
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