Reactions of unsaturated amides under hydroformylation conditions

L. Kollár, Giambattista Consiglio, Piero Pino

Research output: Contribution to journalArticle

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Abstract

N,N-diethyl methacrylamide (1) undergoes hydroformylation, followed by subsequent reactions, under "oxo" conditions involving use of Rh4(CO)12 or Rh4(CO)12 in the presence of (R,R)-Diop (Diop = 2,2-dimethyl-1,3-dioxolane-4,5-diylbis (methylene)bis(diphenylphosphine)) as the catalyst precursor. The product first formed arises from formylation at the unsubstituted unsaturated carbon atom, and subsequently gives α-methyl-γ-butyrolactone (1b), N,N-diethyl 2-methyl-4-hydroxybutyramide (1e), and N,N-diethyl 1-methyl-3-(diethylamino)butyramide (1f). Hydrogenation of the substrate takes also place. The product distribution can be strongly influenced by the reactions conditions. For N,N,N′,N′-tetraethyl itacon-diamide (2) under similar reactions conditions only hydrogenation and isomerization products are formed.

Original languageEnglish
Pages (from-to)389-394
Number of pages6
JournalJournal of Organometallic Chemistry
Volume386
Issue number3
DOIs
Publication statusPublished - Apr 17 1990

Fingerprint

Hydroformylation
Hydrogenation
Carbon Monoxide
Amides
amides
Diamide
hydrogenation
products
Isomerization
Carbon
methylene
Atoms
isomerization
Catalysts
Substrates
catalysts
carbon
atoms
formal glycol
butyramide

ASJC Scopus subject areas

  • Biochemistry
  • Chemical Engineering (miscellaneous)
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Science (miscellaneous)
  • Materials Chemistry

Cite this

Reactions of unsaturated amides under hydroformylation conditions. / Kollár, L.; Consiglio, Giambattista; Pino, Piero.

In: Journal of Organometallic Chemistry, Vol. 386, No. 3, 17.04.1990, p. 389-394.

Research output: Contribution to journalArticle

Kollár, L. ; Consiglio, Giambattista ; Pino, Piero. / Reactions of unsaturated amides under hydroformylation conditions. In: Journal of Organometallic Chemistry. 1990 ; Vol. 386, No. 3. pp. 389-394.
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