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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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 |
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Chemistry and Biology of Carbohydrates
Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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