Reaction of aromatic diamines with diphenylcarbonate catalyzed by phosphorous acids: a new clean synthetic route to mono- and dicarbamates

被引：35

作者：

Aresta, M

Dibenedetto, A

Quaranta, E

机构：

[1] Univ Bari, Dipartmento Chim, I-70126 Bari, Italy

[2] Ctr CNR, MISO, I-70126 Bari, Italy

来源：

TETRAHEDRON | 1998年 / 54卷 / 46期

关键词：

D O I：

10.1016/S0040-4020(98)00873-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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'-methylendianiline (MDA) or 2,4-diaminotoluene (TDA), react with diphenylcarbonate (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 carbamate 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.

引用

页码：14145 / 14156

页数：12

共 34 条

[1] ESTERS OF CARBAMIC ACID
ADAMS, P
BARON, FA
[J]. 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
ARESTA, M
BERLOCO, C
QUARANTA, E
[J]. 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
ARESTA, M
QUARANTA, E
[J]. 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
ARESTA, M
QUARANTA, E
[J]. 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
ARESTA, M
QUARANTA, E
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (12): : 1893 - 1899
[7] MECHANISTIC STUDIES ON THE ROLE OF CARBON-DIOXIDE IN THE SYNTHESIS OF METHYLCARBAMATES FROM AMINES AND DIMETHYLCARBONATE IN THE PRESENCE OF CO2
ARESTA, M
QUARANTA, E
[J]. TETRAHEDRON, 1991, 47 (45) : 9489 - 9502
[8] ARESTA M, 1988, Patent No. 1198206
[9] ARESTA M, 1993, Patent No. 1237207
[10] ARESTA M, 1993, Patent No. 1237208

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