666234-89-5Relevant academic research and scientific papers
Practical β-lactone synthesis: Epoxide carbonylation at 1 atm
Kramer, John W.,Lobkovsky, Emil B.,Coates, Geoffrey W.
, p. 3709 - 3712 (2006)
A readily prepared bimetallic catalyst is capable of effecting epoxide carbonylation to produce β-lactones at substantially lower CO pressures than previously reported catalyst systems. A functionally diverse array of β-lactones is produced in excellent yields at CO pressures as low as 1 atm. This procedure allows for epoxide carbonylation on a multigram scale without the requirement of specialized, high-pressure equipment.
Low pressure carbonylation of heterocycles
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Page/Page column 4, (2008/06/13)
Heterocycles, e.g., epoxides, are carbonylated at low pressure with high percentage conversion to cyclic, ring expanded products using the catalyst where L is tetrahydrofuran (THF).
A new multicomponent reaction catalyzed by a [Lewis acid] +[Co(CO)4]- catalyst: Stereospecific synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO
Church, Tamara L.,Byrne, Christopher M.,Lobkovsky, Emil B.,Coates, Geoffrey W.
, p. 8156 - 8162 (2008/02/08)
The use of mechanistic information to develop a new, catalytic multicomponent reaction is described. The complex [(salph)AI(THF) 2]+[Co(CO)4]- (1, salph = N,N′-o-phenylenebis(3,5-di-tert-butyl-salicylideneimine), THF = tetrahydrofuran), which is known to carbonylate epoxides, aziridines, and β-lactones, was used to catalyze the synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO. Under optimized conditions, the reaction was both selective and high-yielding. 1,3-Oxazinane-2,4-diones were synthesized from a variety of epoxides and isocyanates, including some epoxides that do not undergo simple ring-expansion carbonylation. The best results were obtained using highly electrophilic isocyanates. The mechanism of the multicomponent reaction was investigated using labeling and stereochemistry, and the data obtained were consistent with the 1-catalyzed formation of β-lactone and 1,3-oxazinane-2,4-dione from a common intermediate.
