Harold W. Pinnick

Facile conversion of thioamides into amides

Abstract Thioamides react with m -chloroperoxybenzoic acid (MCPBA) to give good yields of the corresponding amides.

Synthesis of 4-alkoxy-Δ3-pyrrolin-2-ones and tetramic acids

Abstract Acetoacetic ester is converted into 4-alkoxy-Δ3-pyrrolin-2-ones which can be hydrolyzed to give tetramic acids.

A short synthesis of (±)-mesembrine

Abstract An efficient synthesis of (±)-mesembrine and (±)-desdimethoxymesembrine from N-methyl-2-pyrrolidone is reported.

Preparation of Ethyl Hypophosphite1,2

Abstract We report a convenient synthesis of ethyl hypophosphite by the O-alkylation of sodium hypophosphite (eq 1). Thus, when sodium hypo-phosphite is allowed to react with triethyloxonium tetrafluoroborate in methylene chloride at 0°, simple filtration from the inorganic salts and evaporation of the solvent gives the pure ester in 80% yield. This simple preparation employs readily available starting materials3.

Oxidation Adjacent to Nitrogen

Oxidation of carbon adjacent to nitrogen refers to the introduction of either an oxygen atom or a carbon atom next to a nitrogen atom, since either raises the oxidation state of the carbon atom attached to the nitrogen group. Sometimes, the nitrogen functionality is then lost on work-up or in a further hydrolysis step.