Radical ion probes. 11. Reaction of 1,1-dimethyl-5,7-di-t-butylspiro[2.5]octa-4,7-dien-6-one with 5-hexenyl magnesium bromide

Authors

Jason G. Gillmore, Virginia Polytechnic Institute and State UniversityFollow
James M. Tanko, Virginia Polytechnic Institute and State University

Document Type

Article

Publication Date

11-1-1998

Volume Number

39

Issue Number

48

First Page

8795

Last Page

8798

Publisher

Elsevier

ISSN

0040-4039

Comments

This article was published while author Jason G. Gillmore was at the Virginia Polytechnic Institute and State University

Abstract

In an ongoing effort to establish 1,1-dimethyl-5,7-di-t-butylspiro[2.5]octa-4,7-dien-6-one (1) as a mechanistic probe for the detection of single electron transfer (SET), the reaction of1 with 5-hexenyl magnesium bromide was examined in the hopes of observing cyclization of any intermediate 5-hexenyl radicals to cyclopentylcarbinyl radicals. A polar process dominated the reaction, but in the less prevalent SET process, the 5-hexenyl → cyclopentylcarbinyl rearrangement was extensive, indicative of freely diffusing paramagnetic intermediates.

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