Conformational Effects in Free-Radical Hydrogen Abstraction from Medium-Ring Cycloalkanes

Document Type

Article

Publication Date

1-7-1974

Abstract

The case of free-radical hydrogen abstraction from cycloalkanes containing from 5 to 12 carbon atoms is compared with the reactivity of open-chain methylene groups. Activation energies for abstraction from open-chain positions are generally larger than those for all the cycloalkanes studied except cyclohexane. The results are discussed in terms of the release or aggravation of conformational strain upon forming the sp² radical center and, for the C(5)-C(12) compounds, of the inaccessibility of the C-H bonds toward attack. A recent proposal that the relative ease of forming primary, secondary, and tertiary free radicals is predominately steric in origin is discussed.

Department

Chemistry and Geology

Print ISSN

0022-3253

Publication Title

Journal of Organic Chemistry

DOI

10.1021/jo00929a032

Link to Full Text

Share

COinS