Bromonitromethane, a versatile electrophile: Reactions with thiolates

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 15, 1983, Pages 834-835

  Fishwick, Brian R ^a   Rowles, David K ^b   Stirling, Charles J M ^b  

^a AKZO NOBEL CENTRAL RESEARCH   (Netherlands)

^b BANGOR UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049107760     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/c39830000834     Document Type: Article

References (8)

1. W. R. Bowman and G. D. Richardson, Tetrahedron Lett., 1981, 22, 1551.
2. G. A. Russell, M. Jawdosiuk, and F. Ros, J. Am. Chem. Soc, 1979, 101 3378.
3. E.g., W. Ried and L. Kaiser, Synthesis, 1976, 120, and references cited.
4. S. Rajappa and R. Sreenivasan, Indian J. Chem., Sect. B, 1978, 16, 752.
5. C. J. M. Stirling, J. Chem. Soc, 1957, 3597.
6. G. A. Jones, N. G. Bromby, and C. J. M. Stirling, J. Chem. Soc, Perkin Trans. 2, 1983, 385.
7. D. E. L. Carrington, K. Clarke, and R. M. Scrowston, J. Chem. Soc. (C), 1971, 3903. These authors obtained the benzothiophene in 42% yield from the thiol. Generation of the thiol from 2-(2-cyanoethylthio)benzonitrile with base in presence of bromonitromethane gave an 84% yield.
8. G. A. Russell, B. Mudryk, F. Ros, and M. Jawdosiuk, Tetrahedron, 1982, 38, 1059.