title: Iron(II)-catalyzed sulfimidation and [2,3]-sigmatropic rearrangement of propargyl sulfides with tert-butoxycarbonyl azide. Access to N-allenylsulfenimides.
abstract: The iron(II)-catalyzed Bach reaction of tert-butoxycarbonyl azide (BocN(3)) and allyl sulfides has been extended to include propargyl sulfides, which give N-allenylsulfenimide products. Using 10 mol % dppeFeCl(2) as catalyst the reaction proceeds at 0 degrees C with a number of different propargyl sulfides in 31-73% isolated yield. The reaction is limited by product instability toward catalyst and termination of the catalytic cycle by excess BocN(3). N-Allenylsulfenimide 2b smoothly undergoes catalytic hydrogenation and a Diels-Alder reaction with cyclopentadiene.
authors.affiliation: Department of Chemistry, University of California, Irvine, CA 92697, USA.
authors.forename: James P
authors.initials: JP
authors.lastname: Bacci
authors.forename: Kevin L
authors.initials: KL
authors.lastname: Greenman
authors.forename: David L
authors.initials: DL
authors.lastname: Van Vranken