420131-99-3Relevant academic research and scientific papers
Electrochemically induced oxidative S-O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazoles
Terent'ev, Alexander O.,Mulina, Olga M.,Parshin, Vadim D.,Kokorekin, Vladimir A.,Nikishin, Gennady I.
, p. 3482 - 3488 (2019)
The process of oxidative S-O coupling under the action of electric current was developed. Aryl, hetaryl and alkyl sulfonyl hydrazides and N-hydroxy compounds (N-hydroxyimides and N-hydroxybenzotriazoles) are applied as starting reagents for the preparation of sulfonates. The reaction is carried out under constant current conditions in an experimentally convenient undivided electrochemical cell equipped with a graphite anode and a stainless steel cathode under a high current density (60 mA cm?2). NH4Br in this process acts as a supporting electrolyte and participates in the oxidation of the starting compounds to form a coupling product. The developed strategy represents a quite atom-efficient approach: one partner loses two nitrogen and three hydrogen atoms, while another one loses only one hydrogen atom. Cyclic voltammetry and the control experiment allowed us to propose possible reaction pathways: generated through anodic oxidation molecular bromine or its higher oxidation state derivatives oxidize the starting compounds to form reactive species, which couple to form the S-O bond.
Studies on the Lossen-type rearrangement of N-(3-phenylpropionyloxy) phthalimide and N-tosyloxy derivatives with several nucleophiles
Chanmiya Sheikh,Takagi, Shunsuke,Ogasawara, Asako,Ohira, Masayuki,Miyatake, Ryuta,Abe, Hitoshi,Yoshimura, Toshiaki,Morita, Hiroyuki
supporting information; experimental part, p. 2132 - 2140 (2010/04/26)
The reaction of N-(3-phenylpropionyloxy)phthalimide (1a) and N-tosyloxy (5a,b) derivatives with nucleophiles was examined and found to give the products via Lossen-type rearrangement. In order to obtain the scope of this reaction mechanism, further studies the reaction of several N-sulfonyloxyimide derivatives with various nucleophiles under similar conditions were carried out and found to afford the corresponding same types of products in high yields.
