QUINONES AND QUINONE METHIDES .4. DIMERIZATION REACTIONS OF 2-PHENYLMETHYL-5-METHOXY-1,4-BENZOQUINONES

被引：17

作者：

JURD, L

ROITMAN, JN

WONG, RY

机构：

[1] Western Regional Research Laboratory, Science and Education Administration, U.S. Department of Agriculture, Berkeley

来源：

TETRAHEDRON | 1979年 / 35卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)93721-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Base catalyzed dimerization of 2-(4-methoxyphenylmethyl)-5-methoxy-1,4-benzoquinone 6 yields as the chief product an unusual tetrahydroxanthen derivative 7a. The structure of 7a suggests that it is formed by combination of two molecules of the ortho-quinone methide tautomer of 6. Rearrangement of 7a yields the dihydro-oxepin derivative 15 and the indanspirocyclohexene derivatives 17 and 18a, all of which are formed as minor products in the dimerization of 6. In contrast to 6 related 2-(1-phenylethyl)-1,4-benzoquinones do not dimerize in basic media. © 1979.

引用

页码：1041 / 1054

页数：14

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