Radical chemistry based on (+)-cis-pinononic and (+)-cis-pinonic acids

被引:12
作者
Barton, DHR [1 ]
Fontana, G [1 ]
机构
[1] TEXAS A&M UNIV, DEPT CHEM, COLLEGE STN, TX 77843 USA
关键词
D O I
10.1080/00397919608003550
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A high yield method for the preparation of (+)-cis-pinononic acid starting from the inexpensive (+)-alpha-pinene has been developed. The capture of the cyclobutyl radical from decarboxylation of (+)-cis-pinononic acid has been investigated. Moreover the radical decarboxylation of (+)-cis-pinonic acid to the corresponding nor-alkane was studied.
引用
收藏
页码:1953 / 1968
页数:16
相关论文
共 41 条
[1]  
Barton D. H. R., 1990, Aldrichimica Acta, V23, P3
[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]   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
[4]   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
[5]   A PRACTICAL ALTERNATIVE TO THE HUNSDIECKER REACTION [J].
BARTON, DHR ;
CRICH, D ;
MOTHERWELL, WB .
TETRAHEDRON LETTERS, 1983, 24 (45) :4979-4982
[6]   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
[7]   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
[8]   INVENTION OF NEW REACTIONS USEFUL IN THE CHEMISTRY OF NATURAL-PRODUCTS [J].
BARTON, DHR ;
ZARD, SZ .
PURE AND APPLIED CHEMISTRY, 1986, 58 (05) :675-684
[9]   AN UNUSUAL REACTION BETWEEN THE ESTERS OF N-HYDROXY-2-THIOPYRIDONE AND ACTIVATED AZO-COMPOUNDS [J].
BARTON, DHR ;
OZBALIK, N ;
VACHER, B .
TETRAHEDRON, 1988, 44 (24) :7385-7392
[10]   RADICAL CHEMISTRY BASED ON (+)-CIS-PINONIC ACID [J].
BARTON, DHR ;
OZBALIK, N ;
SCHMITT, M .
TETRAHEDRON LETTERS, 1989, 30 (25) :3263-3266