Issue 10, 1984
From the journal:

Journal of the Chemical Society, Chemical Communications

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

Bernard J. Banks,   Anthony G. M. Barrett  and  Mark A. Russell  

Abstract

Acetaldehyde and isobutyraldehyde, RCHO, reacted with phenylthionitromethane (KOH, MeOH) followed by methanesulphonyl chloride (Et3N, CH2Cl2) to give the alkenes, RCH[double bond, length as m-dash]C(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%).

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Article information

DOI
https://doi.org/10.1039/C39840000670
Article type
Paper

J. Chem. Soc., Chem. Commun., 1984, 670-671

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

B. J. Banks, A. G. M. Barrett and M. A. Russell, J. Chem. Soc., Chem. Commun., 1984, 670 DOI: 10.1039/C39840000670

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