Aza-pinacol rearrangement: acid-catalyzed rearrangement of aziridines to imines.
A series of di-, tri-, and tetra-substituted N-tosylaziridines [N-(toluene-p-sulfonyl)aziridines] 1, prepared by aziridination of the corresponding alkenes with N-[(tolyl-p-sulfonyl)imino]phenyliodinane (TsN = IPh), was found to undergo a BF3-catalyzed rearrangement (aza-pinacol rearrangement) under mild conditions to give the corresponding N-tosylimines 2 generally in satisfactory yields.
Sugihara
Yoshiaki
Y
Department of Chemistry, Faculty of Science, Saitama University, Saitama, Saitama 338-8570, Japan.
Iimura
Shinya
S
Nakayama
Juzo
J