Synthesis of chromans by photosensitized electrochemical oxidation of sulfides mediated by methylene blue

被引：24

作者：

Chiba, K ^{[1
]}

Yamaguchi, Y ^{[1
]}

Tada, M ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Bioorgan Chem Lab, Fuchu, Tokyo 1838509, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 49期

关键词：

electrochemical reactions; chromans; sulfides; photochemistry;

D O I：

10.1016/S0040-4039(98)02048-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

o-Quinone methides were generated by a photosensitized cleavage of sulfides under neutral conditions using visible light provided by a 100 Watt spot light and methylene blue as a sensitizer. The key step in the oxidative cleavage is the transfer of one electron form the sulfide to the electronically excited visible dye. The resulting phenylthio radical cation undergoes frangmentation, and the correspondign o-quinone methides are generated and trapped by varied alkenes to yield chromans. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9035 / 9038

页数：4

共 8 条

[1] Stereoselective Diels-Alder reaction of electrogenerated quinones on a PTFE-fiber coated electrode in lithium perchlorate nitromethane [J].