Photolysis of dimethylcarbamoyl azide in the presence of a cyclic aminimide

Harry H. Gibson, Keith Weissinger, Aida Abashawl, Greg Hall, Tom Lawshae, Kirk LeBlanc, Jay Moody, Walter Lwowski

Research output: Contribution to journalArticlepeer-review

Abstract

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 from 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.

Original languageEnglish (US)
Pages (from-to)3858-3861
Number of pages4
JournalJournal of Organic Chemistry
Volume51
Issue number20
StatePublished - 1986
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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