Alkoxy radical accelerated β-fragmentation of alcohols and lactols

被引:9
作者
Rigby, JH [1 ]
Payen, A [1 ]
Warshakoon, N [1 ]
机构
[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
基金
美国国家卫生研究院;
关键词
fragmentation reactions; radicals and radical reactions; alcohols; alkenes;
D O I
10.1016/S0040-4039(01)00121-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of alcohols and lactols with Pb(OAc)(4)/Cu(OAc)(2) in refluxing benzene provides the corresponding delta -unsaturated carbonyl products. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2047 / 2049
页数:3
相关论文
共 21 条
[1]  
Arrmas P., 1993, TETRAHEDRON LETT, V34, P7331
[2]   SYNTHESIS OF MEDIUM-SIZED LACTONES - IODOSOBENZENE DIACETATE AN EFFICIENT REAGENT FOR BETA-FRAGMENTATION OF ALKOXY RADICALS [J].
FREIRE, R ;
MARRERO, JJ ;
RODRIGUEZ, MS ;
SUAREZ, E .
TETRAHEDRON LETTERS, 1986, 27 (03) :383-386
[3]   SYNTHESIS, STRUCTURE AND REACTIONS OF SECOSTEROIDS CONTAINING A MEDIUM-SIZED RING .18. CONFORMATIONS OF THE 10-MEMBERED RING IN 5,10-SECOSTEROIDS .3. (Z)-3-BETA-HYDROXY-5 AND (Z)-3-ALPHA-HYDROXY-5,10-SECO-1(10)-CHOLESTEN-5-ONE ESTERS AND (Z)-5,10-SECO-1(10)-CHOLESTENE-3,5-DIONE [J].
FUHRER, H ;
LORENC, L ;
PAVLOVIC, V ;
RIHS, G ;
RIST, G ;
KALVODA, J ;
MIHAILOVIC, ML .
HELVETICA CHIMICA ACTA, 1981, 64 (03) :703-715
[4]   REACTIONS OF LEAD TETRA-ACETATE .I. REACTIONS WITH SOME BENZENOID COMPOUNDS [J].
HARVEY, DR ;
NORMAN, ROC .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (DEC) :4860-&
[5]   OXIDATION BY METAL SALTS .7. SYNTHESES BASED ON SELECTIVE OXIDATION OF ORGANIC FREE RADICALS [J].
HEIBA, EI ;
DESSAU, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (02) :524-&
[6]  
KAPUSTINA NI, 1984, IAN SSSR KH, P2721
[7]  
KAPUSTINA NI, 1988, IAN SSSR KH, P2327
[8]   A NEW ROUTE TO GAMMA-SUBSTITUTED GAMMA-LACTONES AND DELTA-SUBSTITUTED DELTA-LACTONES BASED ON THE REGIOSELECTIVE BETA-SCISSION OF ALKOXYL RADICALS GENERATED FROM TRANSANNULAR HEMIACETALS [J].
KOBAYASHI, K ;
SASAKI, A ;
KANNO, Y ;
SUGINOME, H .
TETRAHEDRON, 1991, 47 (35) :7245-7258
[9]   1,5-DISUBSTITUTED CYCLOOCTATETRAENES [J].
LYTTLE, MH ;
STREITWIESER, A ;
MILLER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2331-2335
[10]  
Mihailovic M. Lj., 1970, SYNTHESIS, V1970, P209