92643-58-8Relevant articles and documents
Behavior of Benzyl Sulfoxides toward Acid Chlorides. Useful Departures from the Pummerer Reaction
Chupp, John P.,Balthazor, Terry M.,Miller, Michael J.,Pozzo, Mark J.
, p. 4711 - 4716 (2007/10/02)
The present study extends the reaction of certain electrophilic reagents with electron-rich sulfides and sulfoxides beyond previously known limits.Thus, treatment of methoxy- and, more particularly, aminobenzyl sulfoxides 2 with acyl or hydrogen chlorides gives rise in high yields to the corresponding benzyl chlorides, a departure from the normally expected Pummerer reaction.It is demonstrated that ideal substrates for this reaction are o-anilines 1 derived from the well-known rearrangment of aromatic sulfilimines.Further, certain of the o-ammoniobenzyl chloride salts 4 so produced provide a basis for a novel and superior desulfurization of 1 to the corresponding o-methylaniline without resorting to Raney nickel.
