Photolysis of Dimethylcarbamoyl Azide in the Presence of a Cyclic Aminimide

Article abstract of DOI:10.1021/jo00370a020

Dimethylcarbamoyl azide has been photolyzed in the presence of methyl isocyanate to produce the cyclic aminimide 1,1,4-trimethyl-1,2,4-triazolidine-3,5-dione 1,2-ylide (6) and the azo compound N-(dimethylcarbamoyl)-N,N'N'-trimethylazodicarboxamide (7).The azo compound 7 arises a photolytic reaction between dimethylcarbamoyl azide and aminimide 6.Mechanistic studies support a reaction path involving intermolecular-assisted loss of nitrogen from the azide as a result of interaction with aminimide 6.