Cyclopropyl activation of adjacent methylene groups in spiro[2.n]alkanes and bicyclo[n.1.0]alkanes

Charles Roberts, John C. Walton*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The hydrogens at C(2) in spiro[2.n]alkanes are abstracted about five times more rapidly than 'normal' secondary hydrogens by t-butoxyl radicals, because of favourable overlap of the p-orbital at C(2) with the HOMO of the adjacent cyclopropyl ring; the hydrogens at C(2) in bicyclo[n.1.0]alkanes are less activated because the cyclopropyl ring orientation is less favourable for overlap.

Original languageEnglish
Pages (from-to)1109-1111
Number of pages3
JournalJournal of the Chemical Society, Chemical Communications
Issue number16
DOIs
Publication statusPublished - 1 Jan 1984

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