ACIDITY OF BENZOYLCARBAMATES IN DIMETHYL-SULFOXIDE - CONFIRMATION OF MIXED N/O ALKYLATION IN THE MITSUNOBU REACTION

被引：24

作者：

KOPPEL, I

KOPPEL, J

KOPPEL, I

LEITO, I

PIHL, V

WALLIN, A

GREHN, L

RAGNARSSON, U

机构：

[1] TARTU UNIV, DEPT ANALYT CHEM, 2400 TARTU, ESTONIA

[2] UNIV UPPSALA, CTR BIOMED, DEPT BIOCHEM, S-75123 UPPSALA, SWEDEN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1993年 / 04期

关键词：

D O I：

10.1039/p29930000655

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Seventeen benzoyl-, 4-methoxybenzoyl- and 4-nitrobenzoyl-carbamates have been synthesized via their corresponding isocyanates and their acidities determined in dimethyl sulfoxide solution. Their pK(a) values span an interval of nearly 5 pK units (10.4-15.2). Selected derivatives have been investigated as amine synthons in the Mitsunobu reaction. In all cases mixtures of N- and O-alkylated products are obtained.

引用

收藏

页码：655 / 658

页数：4

相关论文

共 19 条

[1]

Albert A., 1962, IONIZATION CONSTANTS

[2] ISOCYANATES .3. BENZOYL ISOCYANATE [J].

ARCUS, CL ;

PRYDAL, BS .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (MAR) :1091-1093

[3] ALPHA,ALPHA,ALPHA-TRICHLOROMETHYLCARBONYL COMPOUNDS AS ACYLATING REAGENTS OF AMIDES [J].

ATANASSOVA, IA ;

PETROV, JS ;

OGNJANOVA, VH ;

MOLLOV, NM .

SYNTHETIC COMMUNICATIONS, 1990, 20 (14) :2083-2090

[4] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463

[5] DIRECT SYNTHESIS OF N-PROTECTED CHIRAL AMINO-ACIDS FROM IMIDODICARBONATES EMPLOYING EITHER MITSUNOBU OR TRIFLATE ALKYLATION - FEASIBILITY STUDY USING LACTATE WITH PARTICULAR REFERENCE TO N-15-LABELING [J].

DEGERBECK, F ;

FRANSSON, B ;

GREHN, L ;

RAGNARSSON, U .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (02) :245-253

[6]

Gibson M.S., 1968, ANGEW CHEM-GER EDIT, V80, P986

[7] GABRIEL SYNTHESIS OF PRIMARY AMINES [J].

GIBSON, MS ;

BRADSHAW, RW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (12) :919-&

[8] SELECTIVE CLEAVAGE OF BOC-ACYLAMIDES - A NOVEL-APPROACH TO DEACYLATION OF CARBOXAMIDES [J].

GREHN, L ;

GUNNARSSON, K ;

RAGNARSSON, U .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1987, 41 (01) :18-23

[9] SYNTHESIS AND USE OF BENZYL TERT-BUTYL IMINODICARBONATE, A VERSATILE REAGENT FOR THE PREPARATION OF AMINES [J].

GREHN, L ;

RAGNARSSON, U .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1988, 53 (11B) :2778-2786

[10] ACIDITY OF IMIDODICARBONATES AND TOSYLCARBAMATES IN DIMETHYL-SULFOXIDE - CORRELATION WITH YIELDS IN THE MITSUNOBU REACTION [J].

KOPPEL, I ;

KOPPEL, J ;

DEGERBECK, F ;

GREHN, L ;

RAGNARSSON, U .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) :7172-7174