
TY  - JOUR
A1  - Ferber, PH 
A1  - Gream, GE 
A1  - Stoneman, TI 
T1  - The 9-Decalyl and Related cations VII. Solvolysis of 3-(Cyclohex-1&#8242;-enyloxy)propyl <i>p</i>-Nitrobenzenesulfonate
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1985
VL  - 38
IS  - 5
SP  - 699
EP  - 711
KW  - 
UR  - https://doi.org/10.1071/CH9850699 
N2  - The solvolysis of 3-(cyclohex-1&#8242;-enyloxy) propyl p- nitrobenzenesulfonate (5) in ethanol buffered separately with sodium ethoxide and triethylamine and 2,2,2-trifluoroethanol buffered with triethylamine has been investigated. Kinetic determinations and product studies have been carried out.  In ethanol buffered with sodium ethoxide , &#960;-bond participation in the above ester occurs to the extent of 30%; this is raised to 84% when triethylamine is used as the buffering agent. With buffered trifluoroethanol as solvent, &#960;-bond participation in the ester is complete; kunsat/ksat = 920 and a quantitative yield of cyclized products is obtained. Kinetic evidence indicates a lack of significant involvement of a lone pair on oxygen (enol ether system) in the solvolysis of the sulfonate ester; in trifluoroethanol , the compound solvolyses only 1.15 times more rapidly than does 4-(cyclohex-1&#8242;-enyl)butyl p-nitrobenzenesulfonate (2), its carbon analogue. 
ER  -

