COMPETITIVE EPOXIDATION AND QUINONE FORMATION IN THE DIMETHYLDIOXIRANE OXIDATION OF DIAZOQUINONES AS AMBIDENT NUCLEOPHILES

被引：3

作者：

ADAM, W

HADJIARAPOGLOU, L

MIELKE, K

TREIBER, A

机构：

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

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)77264-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In addition to the expected dimethyldioxirane (DMD) oxidation of diazoquinones 1 to their quinones 2, the corresponding epoxy quinones 3 are formed directly and not as secondary overoxidation products of the quinones 2 since the latter are persistent rewards DMD under these conditions; this novel oxidation is rationalized in terms of the ambident nucleophilic native of the diazoquinones and corroborated by MO (AM1) calculations.

引用

页码：5625 / 5628

页数：4

共 11 条

[1] SYNTHESIS AND FLUORIDE ION-TRIGGERED CHEMILUMINESCENCE (CIEEL MECHANISM) OF SILOXY-SUBSTITUTED BENZOFURAN DIOXETANES [J].