Phenylthionitromethane: a versatile reagent for the conversion of aldehydes into α-substituted S-phenyl thioesters

Abstract

Acetaldehyde and isobutyraldehyde, RCHO, reacted with phenylthionitromethane (KOH, MeOH) followed by methanesulphonyl chloride (Et3N, CH2Cl2) to give the alkenes, RCHC(SPh)NO2; these reacted with the nuclophiles [Nu = NaOMe, NaOPri potassium Phthalimide, CH2FCONHK, p-MeC6H4SO2Na.2H2O, or KCH(CO2Me)2] in N,N-dimethylformamide (DMF), MeOH, or PriOH at –30°C to give, on subsequent ozonolysis (MeOH–DMF; –78°C) the title thioesters, [RCH(Nu)COSPh](46–79%).