Electrodic cleavage of the N–S bond in N-tosylcarboxamides. A new entry to N-unsubstituted lactams

Reactivity of the Electrogenerated O2·−/CO2 System Towards Alcohols

“…Acetonitrile (Riedel-de Haën), N,N-dimethylformamide (DMF; Riedel-de Haën) and tetraethylammonium perchlorate (TEAP; Fluka) were purified as previously described. [10] IR, NMR, HPLC, GC and melting point apparatus were already described. [10] 1 H NMR spectra were recorded as solutions in CDCl 3 , using Me 4 Si as internal standard.…”

“…[10] IR, NMR, HPLC, GC and melting point apparatus were already described. [10] 1 H NMR spectra were recorded as solutions in CDCl 3 , using Me 4 Si as internal standard. HPLC analyses were carried out using a Merck Hibar LiChrocart (250Ϫ4, 5 µm) RP-18 column.…”

Photochemical Desulfonylation ofN-Tosyl Amides by 2-Phenyl-N,N′-­Dimethylbenzimidazoline (PDMBI)

“…10h,i We also found that photoexcited PDMBI could reduce aromatic imines. 11 Since the N-S bond in N-tosyl amides could be broken by electrochemical reduction, 12 it is expected that N-tosyl amides would be deprotected by photoexcited PDMBI. Indeed, irradiation (>300 nm) of N-tosyl amides 1 with PDMBI in wet acetonitrile at ambient temperature afforded the deprotected amides 2 in excellent yields (Scheme 1, Table 1).…”

Electrogenerated Base-Promoted Synthesis of Organic Carbonates from Alcohols and Carbon Dioxide

“…Acetonitrile (Riedel-de Haën), N,N-dimethylformamide (Riedel-de Haën) and tetraethylammonium perchlorate (TEAP, Fluka) were purified as previously described. [10] All the starting materials and dimethyl carbonate 6c are commercially available. -Column chromatography (c.c.)…”