
%0 Journal Article
%A Cain, EN 
%A Solly, RK 
%T Radical stabilization energies : The &#946;-alkoxy group from kinetics of the thermal isomerization of 1-Chloro-4-methoxymethylbicyclo[2,2,0]hexane in the gas and liquid phase
%J Australian Journal of Chemistry
%D 1972/07/01
%V 25
%N 7
%P 1443-1451
%K 
%R https://doi.org/10.1071/CH9721443
%U https://www.publish.csiro.au/paper/CH9721443 
%X The kinetics of the thermal isomerization of 1-chloro-4-methoxymethyl- log(kb/s-1) = (14.1 ± 0.2)-(36.2 ± 0.5)/&#952;where &#952; = 2.303RT kcal/mol and the subscripts g, a, and b refer to the gas phase, nitrobenzene-d5 as solvent, and diphenyl ether as solvent respectively. The Arrhenius parameters are discussed in terms of transition state estimates for a biradical mechanism. With reference to the isomerization of bicyclo[2,2,0]hexane and 1,4 dichlorobicyclo[2,2,O]hexane, the &#945;-methoxymethyl group is shown to destabilize the biradical by 6.1 ± 2.4 kcal/mol by comparison with an &#945;-propyl group. This radical destabilization by the &#946;-ether oxygen atom is explained in terms of the inductive effect of the &#946;-electronegative atom. 
