1,2,3-Triazoles from (Z)-β-(Formyloxy)vinyl Azides and Triethyl Phosphite

DOI: 10.1021/jo00008a020

Source and publish data:

Journal of Organic Chemistry p. 2680 - 2684 (1991)

Update date:2022-08-04

Topics:

Authors:

D'Andrea, Stan V.

Ghosh, Arun

Wang, Wuyi

Freeman, Jeremiah P.

Szmuszkovicz, Jacob

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Article abstract of DOI:10.1021/jo00008a020

(Z)-Sodium enolates of two α-azido ketones are O-formylated with Me3CCO2CHO in high yield to give isolable (Z)-β-(formyloxy)vinyl azides, which are converted to 1,2,3-triazoles under the influence of triethyl phosphite.A mechanism is proposed for triazole formation involving 1,5-electrocyclization of a vinyl phosphazide intermediate.

Full text of DOI:10.1021/jo00008a020

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