On the stereoisomerization of radicals during aliphatic nucleophilic substitutions

Kim Daasbjerg*, Torben Lund, Henning Lund

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review


Bornyl and isobornyl bromide react with an enolate ion 1- to the same products which indicates a stereoisomerization during the aliphatic nucleophilic substitution. Substitution of 1- with a "radical clock" suggests a radical coupling within the solvent cage. Reaction between a radical clock and anion radicals suggests in this case a coupling outside the solvent cage.

Original languageEnglish
JournalTetrahedron Letters
Issue number4
Pages (from-to)493-496
Number of pages4
Publication statusPublished - 1989
Externally publishedYes

Cite this