Lithium dialkylamide induced 1, 4-elimination of methyl o-methylbenzyl ethers: formation and reactions of o-xylylenes

T Tuschka, K Naito, B Rickborn

Index: Tuschka, Theodore; Naito, Katsuyuki; Rickborn, Bruce Journal of Organic Chemistry, 1983 , vol. 48, # 1 p. 70 - 76

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Citation Number: 33

Abstract

Lithium dialkylamide induced 1, 4elimination is shown to be a general reaction of methyl o- methylbenzyl ethers, giving o-xylylenes as reactive intermediates. The fate of the intermediate depends on a variety of factors including the base used, the dienophile employed as solvent, or the presence of a suitably located double bond in the substrate. With lithium diisopropylamide (LDA), a significant reaction forms the amine derived from 1, ...