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
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.
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页码:1041 / 1054
页数:14
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