N. Lebel, L. A. Spurlock
1964
Citations
0
Influential Citations
26
Citations
Journal
Tetrahedron
Abstract
Abstract The syntheses and proof of structure of syn- and anti-bicyclo[3.2.1]oct-2-en-8-olds are desecribed. Kinetic analysis and product determination for the acetolyses of the p-toluenesulfonates were carried out. Only the anti-ester (III) derives significant anchimeric assistance, and the ion generated must be different than the classical 8-bicyclo[3.2.1]oct-2-ene cation presumably formed from the syn-epimer (II). A new type of homoallylic cation is postulated for the solvolysis of anti-bicyclo[3.2.1]oct-2-en-8-yl p-toluenesulfonate. Comparison of these data with that from the 7-norbornenyl homologs allows several conclusions regarding the requirements for effective homoallytic participation.