
%0 Journal Article
%A Beckwith, ALJ 
%A Gream, GE 
%A Struble, DL 
%T Cyclization and cupric-ion oxidation of 4-(Cyclohex-1-enyl)butyl radical
%J Australian Journal of Chemistry
%D 1972/05/01
%V 25
%N 5
%P 1081-1105
%K 
%R https://doi.org/10.1071/CH9721081
%U https://www.publish.csiro.au/paper/CH9721081 
%X 4-(Cyclohex-1-enyl)butyl radical (45), generated by thermolysis of the appropriate diaoyl peroxide (32), or by treatment of 4-(oyclohex-1-enyl)butyl bromide (34) with tributylstannane, readily undergoes intramolecular homolytic addition. The rate constants for the 1,5- and 1,6-modes of oyclization in benzene at 65º have been determined as 3.8 x 104 s-l and 3.2 x 104 s-l respectively. The mechanisms of homolytic addition and of other processes leading to the formation of the observed products are discussed.   Cuprio-ion oxidation of 4-(cyclohex-1-enyl)butyl radical (45) affords mainly 4-(cyclohex-1-enyl)but-1-ene (43); the rate constant for the reaction in benzene at 80º is estimated to be c. 4 x 108 1. mol-1 s-1. Evidence for the intermediacy of organo-copper species in this and related oxidation reactions is presented. 
