Cobalt carbonyl mediated Michael addition: Direct synthesis of esters containing other functional groups from activated olefins

Attila Sisak, F. Ungváry, László Markó

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5 Citations (Scopus)

Abstract

Hydrocarbalkoxylation of acrylonitrile with stoichiometric amounts of alcohols in the presence of catalytic amounts of Co2(CO)8 and pyridine bases leads to 2,4-dicyano-2-methylbutanoic acid esters. The yield of these Michael adducts shows a maximum as a function of the pyridine/cobalt ratio. Analogous reactions using equimolar amounts of alcohol, acrylonitrile, and an other activated olefin result in products with at least three different functional groups. Acrylonitrile with pyH[Co(CO)4] gives (1-cyanoethyl)cobalt tetracarbonyl, which is proposed to be the key intermediate of the hydrocarbalkoxylation. This complex may be deprotonated to a "Michael donor" anion, i.e. the Michael adducts are most probably formed in a cobalt-mediated way. The above catalytic system promoted also the Michael addition of some C-H acids to activated olefins under atmospheric conditions.

Original languageEnglish
Pages (from-to)2508-2513
Number of pages6
JournalJournal of Organic Chemistry
Volume55
Issue number8
Publication statusPublished - 1990

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Acrylonitrile
Alkenes
Cobalt
Functional groups
Esters
Alcohols
Anions
pyridine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Cobalt carbonyl mediated Michael addition : Direct synthesis of esters containing other functional groups from activated olefins. / Sisak, Attila; Ungváry, F.; Markó, László.

In: Journal of Organic Chemistry, Vol. 55, No. 8, 1990, p. 2508-2513.

Research output: Contribution to journalArticle

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