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Synthesis of Isocyanates and Carbodiimides
Author(s) -
Ulrich H.,
Sayigh A. A. R.
Publication year - 1966
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196607041
Subject(s) - phosgene , phosphorus pentachloride , chemistry , thionyl chloride , oxalyl chloride , thiourea , sulfonyl , organic chemistry , aryl , thiazolidine , acyl chloride , alkyl , chloride
The reaction of 1,3‐disubstituted ureas and 1‐arylsulfonyl‐3‐alkylureas with phosgene permits the preparation of a number of isocyanates and sulfonyl isocyanates that had not previously been described, or that were difficult to prepare. 1,3‐Disubstituted thioureas and 1‐aryl‐(or alkyl)sulfonyl‐3‐alkylthioureas give carbodiimides. Thionyl chloride and phosphorus pentachloride react with the urea derivatives in the same way as phosgene. Oxalyl chloride reacts with ureas to form parabanic acid derivatives, whereas with thiourea it gives 2‐imino‐1,3‐thiazolidine‐4,5‐diones, which can isomerize to parabanic acid derivatives.