Rearrangements in the acetolysis of exo-dehydro-2-norbornyl p-bromobenzenesulfonate

Show full item record

Title: Rearrangements in the acetolysis of exo-dehydro-2-norbornyl p-bromobenzenesulfonate
Author: Cristol, Stanley; Morrill, Terence; Sanchez, Robert
Abstract: exo-3-Deuteriodehydro-2-norbornyl p-bromobenzenesulfonate (VIIb) solvolyzes in glacial acetic acid to give about 7 % of an equimolar mixture of exo-3-deuteriodehydro-2-norbornyl acetate (VIId) and 7-deuteriodehydro-2-norbornyl acetate (VIIId), along with about 93 % of deuterated 3-nortricyclyl acetate (IId). The acetolysis is accompanied by a considerably more rapid scrambling of the p-bromobenzenesulfonate by internal return to 7-deuteriodehydro-2-norbornyl p-bromobenzenesulfonate (VIIIb), without attendant formation of deuterated nortricyclyl p-bromobenzenesulfonate (IIb). The data are consistent with the assumption that ion pairs involving a symmetrical nonclassical cation such as IV are produced in the ionization process, or with the assumption that rapidly equilibrating nonsymmetrical cations such as V and VI are involved, but are not consistent with the suggestion made earlier that the nonsymmetrical cation V is formed in the ionization step and isomerizes relatively slowly to its Wagner-Meerwein isomer VI.
Record URI:
Publishers URL:
Date: 1966-07-05

Files in this item

Files Size Format View

An open access version of this file is not available. Check "Publisher URL" field for access

This item appears in the following Collection(s)

Show full item record

Search RIT DML

Advanced Search