
TY  - JOUR
A1  - Cain, EN 
A1  - Solly, RK 
T1  - 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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1972
VL  - 25
IS  - 7
SP  - 1443
EP  - 1451
KW  - 
UR  - https://doi.org/10.1071/CH9721443 
N2  - 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. 
ER  -

