Allylmagnesium Halides Do Not React Chemoselectively because Reaction Rates Approach the Diffusion Limit

Jacquelyne A. Read, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Competition experiments demonstrate that additions of allylmagnesium halides to carbonyl compounds, unlike additions of other organomagnesium reagents, occur at rates approaching the diffusion rate limit. Whereas alkylmagnesium and alkyllithium reagents could differentiate between electronically or sterically different carbonyl compounds, allylmagnesium reagents reacted with most carbonyl compounds at similar rates. Even additions to esters occurred at rates competitive with additions to aldehydes. Only in the case of particularly sterically hindered substrates, such as those bearing tertiary alkyl groups, were additions slower.

Original languageEnglish (US)
Pages (from-to)2300-2305
Number of pages6
JournalJournal of Organic Chemistry
Volume82
Issue number4
DOIs
StatePublished - Feb 17 2017

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Carbonyl compounds
Reaction rates
Bearings (structural)
Aldehydes
Esters
Substrates
Experiments

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Allylmagnesium Halides Do Not React Chemoselectively because Reaction Rates Approach the Diffusion Limit. / Read, Jacquelyne A.; Woerpel, Keith.

In: Journal of Organic Chemistry, Vol. 82, No. 4, 17.02.2017, p. 2300-2305.

Research output: Contribution to journalArticle

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