Homogeneous catalysis: Catalytic intramolecular conversion of 1,4-dialdehydes to. gamma. -lactones

Journal Article · Thu Mar 01 00:00:00 EST 1990 · Organometallics; (USA)

DOI:https://doi.org/10.1021/om00117a006· OSTI ID:6189840

Bergens, S H; Fairlie, D P; Bosnich, B ^[1]

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1. Univ. of Toronto, Ontario (Canada)

A series of catalysts of the type (Rh(diphosphine)(solvent){sub 2}){sup +} (solvent = weakly coordinating solvent) were investigated for converting 1,4-dialdehydes and 1,4-keto aldehydes to the corresponding {gamma}-lactones, the equivalent of the intramolecular Cannizzaro reaction. It was found that a number of these species were very effective catalysts which tolerated a high degree of steric hindrance and transformed the substrates without any detectable enolization. The carbonylated species (Rh(diphosphine)(CO){sub 2}){sup +} and (Rh(diphosphine)(CO)(solvent)){sup +} are ineffective in catalysis and are the side products of intramolecular lactonization. Decarbonylation of the substrate to give these inactive carbonylated species is a minor component of the catalysis with 1,4-dialdehydes but is the major pathway for the lactonization of 1,4-ketoaldehydes. These catalysts provide a practical, mild catalytic method of converting 1,4-dialdehydes to {gamma}-lactones.

• OSTI ID: 6189840
• Journal Information: Organometallics; (USA), Vol. 9:3; ISSN 0276-7333
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ALDEHYDES
CONVERSION
HOMOGENEOUS CATALYSIS
DATA ANALYSIS
EXPERIMENTAL DATA
LACTONES
MEASURING INSTRUMENTS
MEASURING METHODS
RHODIUM COMPLEXES
CATALYSIS
COMPLEXES
DATA
ESTERS
HETEROCYCLIC COMPOUNDS
INFORMATION
NUMERICAL DATA
ORGANIC COMPOUNDS
TRANSITION ELEMENT COMPLEXES
400201* - Chemical & Physicochemical Properties