Selective carbomethoxylation of aromatic diamines with mixed carbonic acid diesters in the presence of phosphorous acids

被引:43
作者
Aresta, M [1 ]
Dibenedetto, A [1 ]
Quaranta, E [1 ]
机构
[1] Univ Bari, Dipartmento Chim, I-70126 Bari, Italy
关键词
D O I
10.1039/a904624k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reactivity of industrially relevant amines, 4,4'-methylenedianiline (MDA) and 2,4-diaminotoluene (TDA), towards methylphenylcarbonate (MPC), in the presence of Ph2P(O)OH, has been investigated. Both MDA and TDA are catalytically and selectively converted into mono- and di-methylcarbamate esters. Under the relatively mild working conditions used, the formation of ureas and/or N-methyl derivatives is totally repressed. The full spectroscopic characterization of the compounds formed upon interaction of amines with Ph2P(O)OH is also reported. The methodology here described also holds for other mono- and di-amines, both aliphatic and aromatic.
引用
收藏
页码:237 / 242
页数:6
相关论文
共 43 条
[1]   ESTERS OF CARBAMIC ACID [J].
ADAMS, P ;
BARON, FA .
CHEMICAL REVIEWS, 1965, 65 (05) :567-&
[2]  
Aresta M, 1997, CHEMTECH, V27, P32
[3]   BIOMIMETIC BUILDING-UP OF THE CARBAMIC MOIETY - THE INTERMEDIACY OF CARBOXYPHOSPHATE ANALOGS IN THE SYNTHESIS OF N-ARYL CARBAMATE ESTERS FROM ARYLAMINES AND ORGANIC CARBONATES PROMOTED BY PHOSPHORUS-ACIDS [J].
ARESTA, M ;
BERLOCO, C ;
QUARANTA, E .
TETRAHEDRON, 1995, 51 (29) :8073-8088
[4]   REACTIVITY OF PHOSPHACARBAMATES - TRANSFER OF THE CARBAMATE GROUP PROMOTED BY METAL ASSISTED ELECTROPHILIC ATTACK AT THE CARBON-DIOXIDE MOIETY [J].
ARESTA, M ;
QUARANTA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4153-4154
[5]   ROLE OF THE MACROCYCLIC POLYETHER IN THE SYNTHESIS OF N-ALKYLCARBAMATE ESTERS FROM PRIMARY AMINES, CO2 AND ALKYL-HALIDES IN THE PRESENCE OF CROWN-ETHERS [J].
ARESTA, M ;
QUARANTA, E .
TETRAHEDRON, 1992, 48 (08) :1515-1530
[6]   ALKALI-METAL-ASSISTED TRANSFER OF THE CARBAMATE GROUP FROM PHOSPHOCARBAMATES TO ALKYL-HALIDES - A NEW EASY WAY TO ALKALI-METAL CARBAMATES AND TO CARBAMATE ESTERS [J].
ARESTA, M ;
QUARANTA, E .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (12) :1893-1899
[7]   Reaction of aromatic diamines with diphenylcarbonate catalyzed by phosphorous acids: a new clean synthetic route to mono- and dicarbamates [J].
Aresta, M ;
Dibenedetto, A ;
Quaranta, E .
TETRAHEDRON, 1998, 54 (46) :14145-14156
[8]   REACTION OF ALKALI-METAL TETRAPHENYLBORATES WITH AMINES IN THE PRESENCE OF CO2 - A NEW EASY WAY TO ALIPHATIC AND AROMATIC ALKALI-METAL CARBAMATES [J].
ARESTA, M ;
DIBENEDETTO, A ;
QUARANTA, E .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1995, (20) :3359-3363
[9]   MECHANISTIC STUDIES ON THE ROLE OF CARBON-DIOXIDE IN THE SYNTHESIS OF METHYLCARBAMATES FROM AMINES AND DIMETHYLCARBONATE IN THE PRESENCE OF CO2 [J].
ARESTA, M ;
QUARANTA, E .
TETRAHEDRON, 1991, 47 (45) :9489-9502
[10]  
ARESTA M, 1988, Patent No. 1198206