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Cycloadditions of methylenecyclopropanes and strained bicyclo[n.1.0]alkanes to radicophilic olefins

✍ Scribed by Armin De Meijere; Horst Wenck; Fereydoun Seyed-Mahdavi; Heinz Günter Viehe; Vincent Gallez; Ihsan Erden

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
486 KB
Volume
42
Category
Article
ISSN
0040-4020

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✦ Synopsis

The methylenecyclopropanes 1, 2, 11 upon reaction with a-donorsubstituted acrylonitriles 3a, 3c gave two types of products, regular [2+21 cycloadducts 6,. 8, 10, 13, 14 and thiacyclopentane derivatives 7, 9. 'Me capto-dative substituted methylenecyclopropane 12 preferentially homodimerized to 15 even In the presence of 2. The capto-dative olefin 3a also added across the central single bonds of a bicyclo[l.l.O.]butane derivative 4b and bicyclo[2.l.Olpentane 5a to yield 16 and 19 via diradical intermediates.

The strained methylenecyclopropane

(1)'

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