gem-Dimethyl Effect in a Grignard Reagent Cyclization-Cleavage Rearrangement

E. Alexander Hill, Daniel C. Link, Peter Donndelinger

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

(2,2-Dimethyl-4-penten-l-yl)magnesium bromide (1) is in equilibrium with its cyclic isomer, [(3,3-dimethylcyclobutyl) methyl]magnesium bromide (2). The equilibrium constant for this cyclization has a value of 2 X 10-3. The gem-dimethyl substitution leads to an increase of a factor of about 22 in the equilibrium constant and also retards the rate of cleavage of 2. The sources of the gem-dimethyl effect in this system are discussed.

Original languageEnglish
Pages (from-to)1177-1182
Number of pages6
JournalJournal of Organic Chemistry
Volume46
Issue number6
DOIs
StatePublished - Mar 1981

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