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)

被引：16

作者：

BARTON, DHR

CHERN, CY

JASZBERENYI, JC

机构：

[1] Department of Chemistry, Texas A and M University, College Station

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(00)61177-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of olefins containing a three carbon atom chain with carbon radicals generated from carboxylic acids furnishes adducts that are precursors of the corresponding two carbon atom longer alpha-keto-acids. The keto-acids are furnishes in high overall yield.

引用

收藏

页码：5017 / 5020

页数：4

相关论文

共 44 条

[1]

ALLEN F, 1955, J AM CHEM SOC, V77, P2891

[2] Additions to the "synthesis with diazo-methane" [J].

Arndt, F ;

Eistert, B ;

Amende, J .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1928, 61 :1949-1953

[3] Diazo methane and o-nitro compounds, IIN-oxy-isatin from o-nitro-benzoyl chloride [J].

Arndt, F ;

Eistert, B ;

Partale, W .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1927, 60 :1364-1370

[4] Syntheses with diazo methane, V: On the reaction of acid chlorides with diazo methane. [J].

Arndt, F ;

Amende, J .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1928, 61 :1122-1124

[5]

Barton D. H. R., 1990, ALDRICHIM ACTA, V23, P3

[6] NEW AND IMPROVED METHODS FOR THE RADICAL DECARBOXYLATION OF ACIDS [J].

BARTON, DHR ;

CRICH, D ;

MOTHERWELL, WB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) :939-941

[7] FORMATION OF CARBON-CARBON BONDS WITH RADICALS DERIVED FROM THE ESTERS OF THIOHYDROXAMIC ACIDS [J].

BARTON, DHR ;

CRICH, D ;

KRETZSCHMAR, G .

TETRAHEDRON LETTERS, 1984, 25 (10) :1055-1058

[8] RADICAL NITRILE TRANSFER WITH METHANESULFONYL CYANIDE OR PARA-TOLUENESULFONYL CYANIDE TO CARBON RADICALS GENERATED FROM THE ACYL DERIVATIVES OF N-HYDROXY-2-THIOPYRIDONE [J].

BARTON, DHR ;

JASZBERENYI, JC ;

THEODORAKIS, EA .

TETRAHEDRON LETTERS, 1991, 32 (28) :3321-3324

[9] RADICAL-ADDITION TO VINYL SULFONES AND VINYL PHOSPHONIUM SALTS [J].

BARTON, DHR ;

TOGO, H ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1985, 26 (51) :6349-6352

[10] A PRACTICAL ALTERNATIVE TO THE HUNSDIECKER REACTION [J].

BARTON, DHR ;

CRICH, D ;

MOTHERWELL, WB .

TETRAHEDRON LETTERS, 1983, 24 (45) :4979-4982

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