ISSN:
1042-7163
Keywords:
Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hc.520060211
Permalink