Reaction of selenium dibromide with divinyl sulfide

Abstract

We found that the reaction of selenium dibromide with divinyl sulfide leads to an earlier unknown heterocyclic compound 5-bromo-2-bromomethyl-1,3thiaselenolane (I) in 80% yield. Selenium dibromide was prepared in situ by the reaction of selenium with bromine in chloroform. 5-Bromo-2-bromomethyl-1,3-thiaselenolane (I). Major diastereomer. Н NMR spectrum, δ, ppm: 3.79– 3.84 m (2Н, СН2Se), 3.86 m (1Н, СН2Br), 3.99 d. d (1Н, СН2Br, J 9.4, J 8.0 Hz), 5.03 t (1H, SСНSe, J 8.0 Hz), 6.10 d.d (1Н, SСНBr, J 3.3, J 3.4 Hz). С NMR spectrum, δ, ppm: 38.47 (CH2Br), 45.97 (CH2Se), 48.18 (SCHSe), 59.69 (SCHBr). Se NMR spectrum, δ, ppm: 410. Minor diastereomer. Н NMR spectrum, δ, ppm: 3.69–3.73 m (2Н, СН2Br), 3.70 m, 3.89 m (2Н, СН2Se), 5.05 t (1H, SСНSe, J 7.9 Hz), 5.91 d. d (1Н, SeСНBr, J 4.1, J 4.3 Hz). С NMR spectrum, δ, ppm: 37.50 (CH2Br), 44.39 (CH2Se), 47.27 (SCHSe), 58.36 (SCHBr). Se NMR, δ, ppm: 415. Found, %: С 15.00; Н 1.69; Br 49.38. C4H6Br2SSe. Calculated, %: С 14.79; Н 1.86; Br 49.18. The NMR spectra were taken on a Bruker DPX-400 instrument in CCl4 at working frequencies of 400.13 (Н, HMDS), 100.61 (С, HMDS), and 76.30 MHz (Se, Me2Se). ACKNOWLEDGMENTS