Abstract
2-Mercaptobenzothiazole has found widespread industrial applications for the vulcanisation of rubber and, more recently, as a key component of the modified Julia olefination reaction. This review surveys the chemistry of 2-mercaptobenzothiazole, including its aromatic substitution reactions, redox chemistry and factors governing the regioselectivity of its alkylation reactions. In addition, the emerging synthetic uses of this heterocycle, including its application to the deoxygenation of epoxides, and the preparation of alkynes, are described.
Keywords: Enantioselective additions, Epoxide deoxygenation, Julia olefination, 2-mercaptobenzothiazole, Tautomerism, Vulcanisation, 2-aminothiophenol, Ethyl Potassium Xanthate, Carbon Disulfide, TAUTOMERIC EQUILIBRIA
Current Organic Chemistry
Title:2-Mercaptobenzothiazole and its Derivatives: Syntheses, Reactions and Applications
Volume: 16 Issue: 13
Author(s): Feng-Ling Wu, Waleed M. Hussein, Benjamin P. Ross and Ross P. McGeary
Affiliation:
Keywords: Enantioselective additions, Epoxide deoxygenation, Julia olefination, 2-mercaptobenzothiazole, Tautomerism, Vulcanisation, 2-aminothiophenol, Ethyl Potassium Xanthate, Carbon Disulfide, TAUTOMERIC EQUILIBRIA
Abstract: 2-Mercaptobenzothiazole has found widespread industrial applications for the vulcanisation of rubber and, more recently, as a key component of the modified Julia olefination reaction. This review surveys the chemistry of 2-mercaptobenzothiazole, including its aromatic substitution reactions, redox chemistry and factors governing the regioselectivity of its alkylation reactions. In addition, the emerging synthetic uses of this heterocycle, including its application to the deoxygenation of epoxides, and the preparation of alkynes, are described.
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Cite this article as:
Wu Feng-Ling, M. Hussein Waleed, P. Ross Benjamin and P. McGeary Ross, 2-Mercaptobenzothiazole and its Derivatives: Syntheses, Reactions and Applications, Current Organic Chemistry 2012; 16 (13) . https://dx.doi.org/10.2174/138527212800840964
DOI https://dx.doi.org/10.2174/138527212800840964 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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