ISSN:
0009-2940
Keywords:
Diazo compounds, metal-catalyzed decomposition
;
Carbonyl ylides
;
Rhodium(II) perfluorobutyrate, catalyst for diazoester decomposition
;
1,3-Dioxolanes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Transition Metal Catalyzed Reactions of Unsaturated α-Diazo-α-(trimethylsilyl)acetates with Carbonyl CompoundsSome reactions of unsaturated α-diazo-α-(trimethylsilyl)acetates with aldehydes or acetone under the catalytic action of rhodium(II) perfluorobutyrate or copper(I) triflate have been investigated. Thus, the allylic ester 6a affords 1,3-dioxolan-4-ones 8 under Rh(II) catalysis; the Cu-catalyzed reaction yields 8, oxirane 9, and the 3-oxabicyclo[3.1.0]hexane 10. The propargylic ester 6b does not react in a clear fashion with benzaldehyde, 1,3-Dioxolanes result from the homoallylic ester 6c and aldehydes, but enol ether 14 from 6c and acetone.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270831
