Free-radical substitution in aliphatic compounds. Part XXVII. Chlorination and bromination of 1-cyanobutane and cyanocyclobutane

D. S. Ashton, H. Singh, J. M. Tedder*, J. C. Walton, E. A. Watt

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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 languageEnglish
Pages (from-to)125-128
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number2
Publication statusPublished - 1 Dec 1973

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