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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The reactions of t-butoxyl with unsaturated hydrocarbons: Structure and reactivity of allylic radicals

MJ Cuthbertson, E Rizzardo and DH Solomon

Australian Journal of Chemistry 36(10) 1957 - 1973
Published: 1983

Abstract

A radical trapping technique employing 1,1,3,3-tetramethylisoindolin-2-yloxy(1) as scavenger has been used to study the reactions of t-butoxy radicals with propene, 2-methylpropene, but-1-ene, (E)- and (Z)-but-2-ene, 3-methylbut-1-ene, buta-1,3-diene and 2-methylbuta-1,3-diene. Relative rates of double bond addition and of allylic hydrogen abstraction have been measured and are discussed, as are the relative stabilities of the products formed. The allylic radicals generated in these systems react with (1) mainly by coupling at the more substituted terminus of the radical π system. Substituent effects on this regioselectivity may be explained in terms of the electrophilicity of (1).

https://doi.org/10.1071/CH9831957

© CSIRO 1983

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