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Methoxycarbonylation of Aliphatic Diamines with Dimethyl Carbonate Promoted by in situ Generated Hydroxide Ion: A Mechanistic Consideration
Author(s) -
Kim Dae Won,
Huh Eun Soo,
Park Sang Do,
Nguyen Ly Vinh,
Nguyen Mai Dao,
Kim Hoon Sik,
Cheong Minserk,
Nguyen Dinh Quan
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900699
Subject(s) - chemistry , hydroxide , dimethyl carbonate , carbonate , catalysis , in situ , carbonate ion , ion , carbonylation , organic chemistry , hydrogen atom abstraction , hydrogen , inorganic chemistry , carbon monoxide
The methoxycarbonylation reactions of aliphatic diamines with dimethyl carbonate are accelerated greatly in the presence of water. Theoretical investigations on the mechanistic aspects of the methoxycarbonylation of 1,6‐hexanediamine strongly suggest that the hydroxide ion, generated in situ from the interaction of 1,6‐hexanediamine with water, is an active catalytic species and plays a pivotal role in the rate‐determining hydrogen abstraction step from the amino group.