An unexpected two-group migration involving a sulfonynamide to nitrile rearrangement. Mechanistic studies of a thermal N --> C tosyl rearrangement.
We report the discovery of the first double-barreled thermal rearrangement of a sulfonynamide and a methoxybenzyl to a nitrile and the first rearrangement of an SO(2) group from sulfonamide to ketoimine. The rearrangement occurs under surprisingly mild conditions (onset at 100 degrees C in the melt). [reaction: see text]
Bendikov
Michael
M
Exotic Materials Institute, Department of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, CA 90095, USA.
Duong
Hieu M
HM
Bolanos
Eduardo
E
Wudl
Fred
F