Two carbon homologation of carboxylic acids using acrylamide as a radical trap

被引:10
作者
Barton, DHR
Liu, WS
机构
[1] Department of Chemistry, Texas A and M University, College Station
关键词
D O I
10.1016/S0040-4039(97)00418-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photolysis of O-acyl derivatives of N-hydroxy-2-thiopyridone in the presence of acrylamide in dichloromethane furnished crystalline 2-(pyridine-2-thiyl)carboxamides. Desulfurization of the latter by nickel boride afforded primary amides in excellent yields. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:2431 / 2434
页数:4
相关论文
共 27 条
[1]   IMINODITHIOCARBONATES AS FORMALDEHYDE IMINE EQUIVALENTS - SEQUENTIAL 2-STEP APPROACH TO LI UNSUBSTITUTED BETA-LACTAMS THROUGH CHROMIUM(0) CARBENE PHOTOCYCLOADDITION NICKEL BORIDE DESULFURIZATION [J].
ALCAIDE, B ;
CASARRUBIOS, L ;
DOMINGUEZ, G ;
SIERRA, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7934-7936
[2]   THE INVENTION OF RADICAL REACTIONS .33. HOMOLOGATION REACTIONS OF CARBOXYLIC-ACIDS BY RADICAL-CHAIN CHEMISTRY [J].
BARTON, DHR ;
CHERN, CY ;
JASZBERENYI, JC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (02) :407-425
[3]   DECARBOXYLATIVE RADICAL-ADDITION TO VINYLSULPHONES AND VINYLPHOSPHONIUM BROMIDE - SOME FURTHER NOVEL TRANSFORMATIONS OF GEMINAL (PYRIDINE-2-THIYL) PHENYLSULPHONES [J].
BARTON, DHR ;
BOIVIN, J ;
CREPON, E ;
SARMA, J ;
TOGO, H ;
ZARD, SZ .
TETRAHEDRON, 1991, 47 (34) :7091-7108
[4]   2 CARBON HOMOLOGATION OF CARBOXYLIC-ACIDS VIA CARBON RADICALS GENERATED FROM THE ACYL DERIVATIVES OF N-HYDROXY-2-THIOPYRIDONE - SYNTHESIS OF CN+2 ALPHA-KETO-ACIDS FROM CN ACIDS - (THE 3 CARBON PROBLEM) [J].
BARTON, DHR ;
CHERN, CY ;
JASZBERENYI, JC .
TETRAHEDRON LETTERS, 1992, 33 (35) :5017-5020
[5]   THE INVENTION OF RADICAL REACTIONS .25. A CONVENIENT METHOD FOR THE SYNTHESIS OF THE ACYL DERIVATIVES OF N-HYDROXYPYRIDINE-2-THIONE [J].
BARTON, DHR ;
SAMADI, M .
TETRAHEDRON, 1992, 48 (35) :7083-7090
[6]   THE INVENTION OF CHEMICAL-REACTIONS - THE LAST 5 YEARS [J].
BARTON, DHR .
TETRAHEDRON, 1992, 48 (13) :2529-2544
[7]   The invention of radical reactions .36. Synthetic studies related to 3-deoxy-D-manno-2-octulosonic acid (KDO) [J].
Barton, DHR ;
Jaszberenyi, JC ;
Liu, WS ;
Shinada, T .
TETRAHEDRON, 1996, 52 (08) :2717-2726
[8]   THE INVENTION OF RADICAL REACTIONS .34. HOMOLOGATION OF CARBOXYLIC-ACIDS TO ALPHA-KETO CARBOXYLIC-ACIDS BY BARTON-ESTER BASED RADICAL-CHAIN CHEMISTRY [J].
BARTON, DHR ;
CHERN, CY ;
JASZBERENYI, JC .
TETRAHEDRON, 1995, 51 (07) :1867-1886
[9]   THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS [J].
BARTON, DHR ;
CRICH, D ;
MOTHERWELL, WB .
TETRAHEDRON, 1985, 41 (19) :3901-3924
[10]  
BARTON DHR, 1991, TETRAHEDRON LETT, V32, P3309