H. Shimizu, A. Sugimoto, T. Kataoka
Mar 1, 1995
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0
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3
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Journal
Heteroatom Chemistry
Abstract
A novel cyclic sulfilimine, 2-methyl-2,4,1-benzodithiazin-2-ium-1-ide (4) was synthesized by deprotonation of the corresponding azasulfonium salt (3) with base. The compound 4 was oxidized with potassium permanganate to afford the sulfoximine 5, exclusively. On refluxing in several solvents, compound 4 underwent a ring contraction to afford benzothiazole (8) via the 1,2-imino shift. The reaction of 4 with a variety of electrophiles, such as dialkyl acetylenedicarboxylate, acylating agents, diphenylcyclopropenone, and phenyl isocyanate, afforded ringopened adducts. Synthetic approaches to cyclic disulfonium ylides are also described.