PHOTOCHEMICAL AND THERMAL REARRANGEMENT OF ACYL-SUBSTITUTED QUINONE METHIDES, ACCESSIBLE BY DIMETHYLDIOXIRANE OXIDATION OF BENZOFURANS AND SUBSEQUENT VALENCE ISOMERIZATION OF THE RESULTING EPOXIDES

被引:5
作者
ADAM, W
SAUTER, M
机构
[1] Institut Für Organische Chemie, Universität Würzburg, Würzburg, D-97074, Am Hubland
关键词
EPOXIDATION; DIOXIRANE; DIMETHYL-; BENZOFURANS; 2-METHYL-3-PHENYL; BENZOFURAN EPOXIDES; QUINONE METHIDES; (Z/E) PHOTOISOMERIZATION; NORCARADIENE; BENZOCYCLOHEPTAFURAN; THERMAL REARRANGEMENT; XANTHENES; 9-ACETYL-;
D O I
10.1002/cber.19931261220
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The photoisomerization of quinone methides 3 to benzocycloheptafuran 4 and the thermolysis of the latter to xanthenes 5 are reported. The quinone methides 3 are accessible by dimethyldioxirane oxidation and subsequent valence isomerization of the resulting benzofuran epoxides 2. On irradiation (lambda > 400 nm), the quinone methides 3 rearrange by cyclization to the corresponding norcaradiene, and ring enlargement affords the benzocycloheptafurans 4. Thermolysis of the cycloheptatrienes 4 leads to the xanthenes 5, first by cycloreversion to the norcaradienes, followed by electrocyclization to the chromenes and tautomerization of the latter. The new cycloheptatrienes 4 and xanthenes 5 were fully characterized.
引用
收藏
页码:2697 / 2699
页数:3
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