Journal of Organic Chemistry p. 1789 - 1792 (1982)
Update date:2022-09-26
Topics:
Boeckman, Robert K.
Demko, Donald M.
The intramolecular Diels-Alder cyclizations of two triene diesters derived from (E)-3,5-hexadienoic acid have been investigated.The cyclizations proceed remarkably sluggishly and only after double-bond isomerization to the sorbate derivative has occurred.The reasons behind this unusual behavior were investigated, and evidence points strongly to the effects of overlap requirements of the ester linkage in the transition state as the major factor.
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Doi:10.1021/op1000836
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