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  • Oxa-ene reaction of enols of amides with 4-phenyl-1,2,4-triazoline-3,5-dione.

Oxa-ene reaction of enols of amides with 4-phenyl-1,2,4-triazoline-3,5-dione.

The Journal of organic chemistry (2007-12-13)
Ahmad Basheer, Zvi Rappoport
ABSTRACT

The reaction of 16 enols of amides with 4-phenyl-1,2,4-triazoline-1,3-dione gave open chain adducts rather than the [2 + 2] cycloadducts with a hemiaminal moiety, both in solid state and in solution. This assignment is based on X-ray crystallography, (1)H and (13)C NMR data, and IR spectra. The suggested mechanism involves hydroxyl proton loss in a formal oxa-ene reaction. Mechanistic details and a possible alternative are discussed.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
4-Phenyl-1,2,4-triazoline-3,5-dione, 97%