THE INFLUENCE OF CAPTODATIVE EFFECT ON THE DIENOPHILICITY OF OLEFINS. THE EASY DIELS-ALDER REACTION OF α-METHYLTHIOACRYLONITRILE WITH CYCLOHEXADIENE

DOI: 10.1016/S0040-4039(01)80848-0

Source and publish data:

Tetrahedron Letters p. 5041 - 5044 (1985)

Update date:2022-08-28

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Authors:

Boucher, Jean-Luc

Stella, Lucien

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Article abstract of DOI:10.1016/S0040-4039(01)80848-0

We show that the cycloaddition of α-methylthioacrylonitrile to cyclohexadiene is faster than that of acrylonitrile.This indicates that the captodative substitution exerts an accelerating effect on the Diels-Alder reaction despite the larger steric bulk of the methylthio group compared to hydrogen.

Full text of DOI:10.1016/S0040-4039(01)80848-0

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