Tetrahedron

Quinones and quinone methides—IV: dimerization reactions of 2-phenylmethyl-5-methoxy-1, 4-benzoquinones

L Jurd, JN Roitman, RY Wong

Index: Jurd,L. et al. Tetrahedron, 1979 , vol. 35, p. 1041 - 1054

Full Text: HTML

Citation Number: 13

Abstract

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 ...