REACTION OF AROMATIC DIAMINES WITH DIPHENYLCARBONATE CATALYZED BY PHOSPHORUS-ACIDS - A NEW CLEAN SYNTHETIC ROUTE TO MONO-CARBAMATES AND DICARBAMATES

Authors
ARESTA M DIBENEDETTO A QUARANTA E
Citation
M. Aresta et al., REACTION OF AROMATIC DIAMINES WITH DIPHENYLCARBONATE CATALYZED BY PHOSPHORUS-ACIDS - A NEW CLEAN SYNTHETIC ROUTE TO MONO-CARBAMATES AND DICARBAMATES, Tetrahedron, 54(46), 1998, pp. 14145-14156
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
46
Year of publication
1998
Pages
14145 - 14156
Database
ISI
SICI code
0040-4020(1998)54:46<14145:ROADWD>2.0.ZU;2-B
Abstract
In the presence of organophosphorus acids [Ph-2(O)OH, (PhO)(2)P(O)OH, (BuO)(2)P(O)OH, (BuO)P(O)(OH)(2)], aromatic diamines, such as 4,4'-met hylendianiline (MDA) or 2,4-diaminotoluene (TDA), react with diphenylc arbonate (DPC) to afford in a very selective way mono- and dicarbamate phenyl esters. The carbamation process is strongly influenced by the temperature and solvent. The influence of both these factors on carbam ate yield and selectivity has been investigated and we present in this study the kinetics of formation of both mono- and dicarbamate esters. (C) 1998 Elsevier Science Ltd. All rights reserved.