gem-Dialkyl effect in the intramolecular Diels-Alder reaction of 2-furfuryl methyl fumarates: the reactive rotamer effect, the enthalpic basis for acceleration, and …

ME Jung, J Gervay

文献索引：Jung, Michael E.; Gervay, Jacquelyn Journal of the American Chemical Society, 1991 , vol. 113, # 1 p. 224 - 232

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被引用次数: 296

摘要

Abstract: Investigation of the rates of cyclization of a series of substituted 2-furfuryl methyl fumarates la-h has allowed us to determine which of the two explanations for the gem-dialkyl effect is more important. Studies with compounds substituted with small-membered rings showed that the rate acceleration is due primarily to the reactive rotamer effect and not to angle compression (" Thorpe-Ingold effect"). For example, the cyclobutyl-substituted ...