The Journal of Organic Chemistry

Stereochemistry of LiNR2-induced 1, 4-elimination of allylic (benzylic) ethers

RJ Moss, B Rickborn

Index: Moss, Randall J.; Rickborn, Bruce Journal of Organic Chemistry, 1986 , vol. 51, # 11 p. 1992 - 1996

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Citation Number: 19

Abstract

The stereochemistry of base-induced 1, Celimination of H, D-substituted allylic (benzylic) ethers is examined. The substrates used are structurally similar (cyclohexenyl systems) but differ significantly in the nature of the “diene” product which is generated, forming naphthalene in one case and a very reactive intermediate o-xylylene in the other. These differences are reflected in the ease of elimination, allowing in the naphthalene-forming ...