The Journal of Organic Chemistry

Electron Transfer Profile of Cyclopropanone Acetals in the Nonirradiated Reaction with Tetracyanoethylene, Chloranil, and Dicyanodichlorobenzoquinone

A Oku, M Abe, M Iwamoto

Index: Oku, Akira; Abe, Manabu; Iwamoto, Masaharu Journal of Organic Chemistry, 1994 , vol. 59, # 24 p. 7445 - 7452

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Citation Number: 17

Abstract

The donor profiles of cyclopropanone acetals 1 and 2 were examined in the reactions with electron acceptors (TCNE, DDQ, chloranil, and 1-cyanonaphthalene). With TCNE under nonirradiating conditions, an exclusive 2+ 2 cycloaddition took place stereospecifically with monosubstituted acetals la-c but nonstereospecifically with disubstituted acetals ld, e. With quinones, a ringopening of the cyclopropane and its coupling with the quinone took place ...