新組み合わせ試薬トリフェニルホスフィン-チオシアノーゲン (TPPT)
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The reactions of triphenylphosphine -thiocyanogen (TPPT), prepared by a combination of equimolar amount of triphenylphosphine and thiocyanogen, with various nucleophiles are reviewed. It can be classified by the following two features: a) as observed in the reaction with alcohols, carboxylic acids, and epoxides, nucleophilic attack on the phosphorus atom of TPPT followed by substitution of the SCN anion on the adjacent carbon to oxygen atom of the intermediate with elimination of triphenylphosphine oxide, giving the thio-and/or isothiocyanates (Type A) and b) as observed in the reaction of amines, organometallic compounds, indoles and pyrroles, nucleophilic addition to the -N=C=S carbon of TPPT, giving thiocarbamoylated compounds (Type B). Synthetic utilities of TPPT are also summarized.
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