Chemistry of dioxine-annelated cycloheptatriene endoperoxides and their conversion into tropolone derivatives: an unusual non-benzenoid singlet oxygen source

被引：13

作者：

Dastan, A ^{[1
]}

Balci, M

机构：

[1] Ataturk Univ, Dept Chem, TR-25240 Erzurum, Turkey

[2] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

来源：

TETRAHEDRON | 2006年 / 62卷 / 17期

关键词：

tropone; tropolone; endoperoxide; singlet oxygen; rearrangement;

D O I：

10.1016/j.tet.2006.02.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chemistry of two bicyclic endoperoxides, obtained by photooxygenation of 2,3-dihydro-7H-cyclohepta[1,4]dioxine and 2,3-dihydro-7H-cyclohepta[b][1,4]dioxin-7-one was investigated with the aim of synthesizing the respective tropolone derivatives. The reaction of these endoperoxides with base, thiourea and their thermolysis provided the desired tropolone derivatives in high yield. On the other hand, the thermolysis of the endoperoxide derived from 2,3-dihydro-7H-cyclohepta[b] [ 1,4]dioxin-7-one underwent an unprecedented route and formed parent Molecule and singlet oxygen instead of the expected troponoids. The formation mechanisms of all products are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4003 / 4010

页数：8

共 68 条

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