Carbon–oxygen bond insertion in the reaction of dialkoxycarbenes with anhydrides
- 1 November 1995
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 1995 (11) , 1907-1914
- https://doi.org/10.1002/jlac.1995199511269
Abstract
Dimethoxycarbene (1a) and methoxy(2,2,2‐trifluoroethoxy)‐carbene (1b) were generated in benzene solution by thermolysis of the corresponding 2,2‐dialkoxyoxadiazolines 7. The carbenes were trapped by intermolecular reaction with a variety of cyclic anhydrides 8. The products 9 are formally the result of carbene insertion into the bond between the carbonyl carbon and the ring oxygen atoms. The results of a competition between dimethylmaleic and dichloromaleic anhydrides for dimethoxycarbene suggests that this reaction proceeds by nucleophilic attack of dialkoxycarbene onto the carbonyl carbon atom of the anhydride.Keywords
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