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A mechanistic study of the selenium‐catalysed carbonylation of secondary amines with carbon monoxide
Author(s) -
Fujiwara ShinIchi,
Miyoshi Noritaka,
Ogawa Akiya,
Kambe Nobuaki,
Sonoda Noboru
Publication year - 1989
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610020407
Subject(s) - chemistry , diselenide , piperidine , selenium , carbon monoxide , carbonylation , amine gas treating , catalysis , aminolysis , phosgene , benzylamine , formamide , organic chemistry , oxygen , photochemistry
The reaction pathway of urea formation by selenium‐catalysed carbonylation of secondary amines with carbon monoxide in the presence of oxygen was studied using piperidine as a secondary amine. It was established that selenium reacts with carbon monoxide and piperidine to give carbamoselenoate as an intermediate, which affords biscarbamoyl diselenide by the oxidation with molecular oxygen. Aminolysis of biscarbamoyl diselenide gives the urea derivative, accompanying the regeneration of selenium catalyst.