title: Direct amination of olefins through sequential triazolinedione ene reaction and carbanion-assisted cleavage of the N-N urazole bond
abstract: [formula: see text] Allylic amines 5 are obtained in 30-55% overall yields by the base-catalyzed hydrolysis of trialkylated allylic urazoles 3; the latter are prepared by the TAD ene reaction of the appropriate olefin and further N-alkylation with alpha-bromoacetophenone. The proposed mechanism for this novel urazole rupture is based on the generation of a carbanion adjacent to the hydrazide functionality, which induces urazole ring-opening by cleavage of the N-N bond.
authors.affiliation: Institute of Organic Chemistry, University of Wurzburg, Germany. adam@chemie.uni-wuerzburg.de
authors.initials: W
authors.lastname: Adam
authors.initials: A
authors.lastname: Pastor
authors.initials: T
authors.lastname: Wirth