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Reactions of Diphenylphosphinothioyl Isothiocyanate and Related Compounds with Some Nucleophiles and Carbodiimides

1973; Oxford University Press; Volume: 46; Issue: 8 Linguagem: Inglês

10.1246/bcsj.46.2559

1348-0634

Iwao Ojima, Kin‐ya Akiba, Naoki Inamoto,

Synthesis of β-Lactam Compounds

Diphenylphosphinothioyl isothiocyanate (1) reacted with alcohols, water and diphenylphosphinothioic acid to give the esters and anhydride of diphenylphosphinothioic acid by substitution reaction on the phosphorus atom, but reacted with amines by addition to the isothiocyanate group to afford diphenylphosphinothioylthioureas or their ammonium salts. Diphenylphosphine and p-toluenethiol, however, did not react with 1. On the contrary, diphenylphosphinothioyl isocyanate underwent only addition reaction with water, amine and thiol. Isothiocyanate (1) and p-toluenesulfonyl isothiocyanate were found to undergo 1,2-cycloaddition reaction with carbodiimides across the C=S bond to produce 1,3-thiazetidine derivatives.