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Carbon–oxygen bond insertion in the reaction of dialkoxycarbenes with anhydrides

✍ Scribed by Pole, David L. ;Warkentin, John

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
881 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

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.

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