Addition of 4- Phenyltriazolinedione toCarbonyl Compounds: The Formation of alpha-Urazolylcarbonyl Compounds

Document Type

Article

Journal/Book Title

Journal of Organic Chemistry

Publication Date

1990

Volume

55

First Page

193

Last Page

197

Abstract

N-Phenyltriazolinedione (PTAD) adds to a variety of carbonyl compounds to form -urazolylcarbonyl compounds. With highly enolized carbonyl systems, this type of substitution reaction can occur rapidly even in the absence of a catalyst. However, with simple carbonyl systems, the reaction is greatly accelerated by an acid catalyst such as trifluoroacetic acid. Unsymmetrical ketones afford isomeric ��- and ��'-urazolyl ketones, and the initially formed monourazoles can be further urazolated to the diurazoles through the application of more than 1 equiv of PTAD.

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