Abstract
1-Cyanobutane and oyanocyclobutane have been chlorinated and brominated in the gas phase over a wide range of temperatures. The results for 1-cyanobutane are compared with previous halogenations of 1-substituted n-butanes. The chlorination of cyanocyclobutane gives a very high trans/cis ratio for the 1-cyano-2-chlorocyclobutane and quite a high trans/cis ratio for the 1,3-product. This is interpreted in terms of an interaction between the π-orbitals of the cyano-group and the half-filled 2p2 atomic orbital of the radical site. The bromination of cyanocyclobutane is accompanied by a small amount of elimination of HCN; this reaction is increased by addition of HBr or by an increase in the surface area.
Original language | English |
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Pages (from-to) | 125-128 |
Number of pages | 4 |
Journal | Journal of the Chemical Society, Perkin Transactions 2 |
Issue number | 2 |
Publication status | Published - 1 Dec 1973 |