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Reaction of benzothiazoline with benzyne - generation of novel heterocyclic sulfur ylide, benzothiazolinium s-ylide

โœ Scribed by Mikio Hori; Tadashi Kataoka; Hiroshi Shimizu; Norihiro Ueda

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
245 KB
Volume
22
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A novel heterocyclic sulfur ylide, 2-t-butyl-3-methyl-1-phenylbenzothiazolinium ylide 13) was generated as an intermediate in the reaction of 2-t-butyl-3-methylbenzothiazolze (2) with benzyne. The S-ylide 13 underwent a novel intermolecular [1,2] shift to give 2-t-butyl-3-methyl-2-phenylbenzothiazomne (3).

Synthesis and rearrangement of benzothiazolinium N-ylides have been reported. K. Akiba,

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## Abstract The unexpected 1,3โ€benzodithiine derivatives **5b,c** were obtained from the reactions of trimethylsilyldiazomethane **2** with __C__โ€sulfonyldithioformates, bearing pentachlorophenylthio group, **1b,c** via unprecedented cyclization of the transient thiocarbonyl ylides **4b,c**. While