Ammonium persulfate activated DMSO as a one-carbon synthon for the synthesis of methylenebisamides and other applications

Abstract

Activation of DMSO to work as an economical and environmentally benign one-carbon synthon has been achieved by using a bench-top reagent ammonium persulfate for general and efficient access to symmetrical methylenebisamides from primary amides.

Ni‐Catalyzed Synthesis of Methylenebisamides: Dual Role of DMSO Both as Methylene Source and Oxidant

“…These results are very good evidences for the mechanism presented in Scheme for the formation of methylene bisbenzamidederivatives . At first stage, hydrolysis of benzonitriles to the corresponding benzamides occurs in the presence of acetic acid to form typical benzamide A .…”

Rechargeable Zn2+/Al3+ dual-ion electrochromic device with long life time utilizing dimethyl sulfoxide (DMSO)-nanocluster modified hydrogel electrolytes

“…1(b), it is possible for the DMSO molecule to polymerize upon interaction with SO 4À radicals simultaneously along two pathways. 48 DMSO can be incorporated into the hydrogel by strong polar interaction or copolymerization (Fig. S2 †).…”

“…S2 †). 48,49 The polar S]O group can form hydrogen bonds with water molecules and, thereby, adhere to the hydrophilic amino group (Fig. S2(a) †).…”

Metal‐Free Synthesis of Methylene‐Bridged Bisamide via Selectfluor‐Mediated Oxidative Methylenation

“…Differing from the 2‐aminobenzamide substrate, 2‐hydroxybenzamide reacted under standard conditions to afford an annulation and methylenation product 7 . In comparison, when ammonium persulphate instead of Selectfluor was used for this reaction according to the reported procedure, the desired product was not obtained. The structures of compounds 5–7 was characterized by NMR and HRMS.…”

“…Dimethyl sulfoxide (DMSO), as a cheap, aprotic polar and versatile solvent with low toxicity and relative stability, has been widely used as a synthon in organic synthesis such as a source of ‐Me, ‐CH, or ‐CHO . In addition, several papers have been reported on the synthesis of bisamides from primary amides using DMSO as a methylene soucre in the presence of an additional oxidant such as ammonium persulfate, cyanuric chloride, I 2 or catalysed by NiCl 2 . On the other hand, Selectfluor as a commercially available electrophilic fluorinating reagent has become one of the most popular reagents to donate fluorine .…”