SYNTHESIS AND PROPERTIES OF A NOVEL CYCLIC SULFILIMINE, 2-METHYL-2,4,1-BENZODITHIAZIN-2-IUM-1-IDE

被引：4
|
作者：
SHIMIZU, H
SUGIMOTO, A
HATAOKA, T
HORI, M
机构：
[1] Gifu Pharmaceutical University, Gifu, 502, -1
来源：
HETEROATOM CHEMISTRY | 1995年 / 6卷 / 02期
关键词：
D O I：
10.1002/hc.520060211
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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 ring-opened adducts. Synthetic approaches to cyclic disulfonium ylides ave also described.
引用
收藏
页码：167 / 176
页数：10
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