PREPARATION OF 2H-BENZOXETES BY PHOTOINDUCED [2+2] CYCLOADDITION OF QUINONE METHIDES, ACCESSIBLE BY DIMETHYLDIOXIRANE (DMD) OXIDATION OF 2,3-DIMETHYLBENZOFURANS

被引：11

作者：

ADAM, W

SAUTER, M

ZUNKLER, C

机构：

[1] Institut Für Organische Chemie, Universität Würzburg, Würzburg, D-97074, Am Hubland

来源：

CHEMISCHE BERICHTE | 1994年 / 127卷 / 06期

关键词：

EPOXIDATION; DIOXIRANE; DIMETHYL; BENZOFURANS, 2,3-DIMETHYL; BENZOFURAN EPOXIDES; QUINONE METHIDES; 2+2] PHOTOCYCLOADDITION; BENZOXETES; HETERO-DIELS-ALDER REACTION;

D O I：

10.1002/cber.19941270622

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Irradiation (lambda > 366 nm) of the quinone methides 3, which were formed by valence isomerization of the methyl-, chloro-, and tert-butyl-substituted 2,3-dimethylbenzofuran epoxides 2, afforded the novel 2H-benzoxetes 4 by photochemical [2 + 2] cycloaddition. These strained and highly labile benzoxetes 4 were spectrally (H-1 and C-13 NMR) characterized at subambient temperatures. On prolonged storage (2-3 d) at -20 to -10-degrees-C, the benzoxetes 4 reverted to the, quinone methides 3 and/or berizofuran epoxides 2.

引用

页码：1115 / 1118

页数：4

共 24 条

[1] DIMETHYLDIOXIRANE EPOXIDATION OF BENZOFURANS - REVERSIBLE THERMAL AND PHOTOCHEMICAL VALENCE ISOMERIZATION BETWEEN BENZOFURAN EPOXIDES, QUINONE METHIDES, AND BENZOXETENES [J].