CYCLOADDITIONS OF METHYLENECYCLOPROPANES AND STRAINED BICYCLO(n.1.0)ALKANES TO RADICOPHILIC OLEFINS

Article abstract of DOI:10.1016/S0040-4020(01)87348-8

The methylenecyclopropanes 1, 2, 11 upon reaction with α-donorsubstituted acrylonitriles 3a, 3c gave two types of products, regular (2+2) cycloadducts 6, 8, 10, 13, 14 and thiacyclopentane derivatives 7, 9.The 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(1.1.0.)butane derivative 4b and bicyclo(2.1.0)pentane 5a to yield 16 and 19 via diradical intermediates.