Recent Advances in the Chemistry of Benzo [b] thiophenes

Abstract

This chapter discusses the molecular structure and physical properties of benzo[b]thiophenes. Molecular orbital calculations are applied to benzo[b]thiophene derivatives. The spectroscopic analysis of benzo[b]thiophenes is provided. The structures of N-(3-phenyl-2-benzo[b]thienyl)benzenecarbothioamide and 5-bromo-2,3-dimethylbenzo[b]thiophene have been established by X-ray crystallography. Crystallographic data are available for the 1:1 molecular complex formed between benzo[b]thiophene-3-carboxaldehyde and l,3,5-trinitrobenzene and for the 1,1-dioxides. Dipole moments of benzo[b]thiophene and of several of its alkyl, phenyl, and 1,1-dioxide derivatives are determined. Miscellaneous reactions and properties of benzo[b]thiophenes are discussed. The miscellaneous reactions include addition reactions, photocyclization reactions, ring-expansion reactions, ring-fission reactions, 2,3-didehydrobenzo[b]thiophene (2,3-benzo[b]thiophyne). The chapter provides a brief survey of the substitution patterns in benzo[b]thiophene and in its derivatives. © 1981, Academic Press Inc.