SENSITIVE NATURE OF LIGAND COUPLING AND PSEUDOROTATION TO ELECTRONIC EFFECT OF SUBSTITUENT---LIGAND COUPLING IN THE REACTIONS OF BENZYLIC ARYL SULFOXIDES WITH BENZYLIC GRIGNARD REAGENTS

DOI: 10.1016/S0040-4039(00)80517-1

Source and publish data:

Tetrahedron Letters p. 4441 - 4444 (1988)

Update date:2022-07-31

Topics:

Authors:

Wakabayashi, Shoji

Ishida, Masahiro

Takeda, Takashi

Oae, Shigeru

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Article abstract of DOI:10.1016/S0040-4039(00)80517-1

Unlike the reaction of benzylic 2-pyridyl sulfoxides with benzylic Grignard reagents, in the reaction of p-benzenesulfonylphenyl benzylic sulfoxides with benzylic Grignard reagents, benzylic groups bearing an electronwithdrawing group tends to couple with the aryl group preferentially.This change is considered to be due to a slight change of electronic environements which would effect on the ease of pseudorotation of the incipient ?-sulfurane formed during the reaction.

Full text of DOI:10.1016/S0040-4039(00)80517-1

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