AN EFFICIENT SYNTHESIS OF LARGE RING ACETYLENES

被引:18
作者
BOIVIN, J
HUPPE, S
ZARD, SZ
机构
[1] ECOLE POLYTECH,CNRS,SYNTH ORGAN LAB,F-91128 PALAISEAU,FRANCE
[2] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1016/0040-4039(95)01146-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The two regioisomeric beta-ketoesters obtained by ring expansion of a cycloalkanone with ethyl diazoacetate and a Lewis acid give the same cycloalkyne upon exposure of the corresponding isoxazolinone to sodium nitrite / aqueous acetic acid and ferrous sulfate.
引用
收藏
页码:5737 / 5740
页数:4
相关论文
共 31 条
[21]   SYNTHESIS AND SOME REACTIONS OF 1,2-CYCLONONADIENE AND 1,2-CYCLODECADIENE [J].
MOORE, WR ;
BERTELSON, RC .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (12) :4182-&
[22]  
NAGAO K, 1983, SYNTHESIS-STUTTGART, P197
[23]  
NAKAGAWA M, 1978, CHEM CARBON CARBON T, P635
[24]   ZUR KENNTNIS DES KOHLENSTOFFRINGES .60. ZUR KENNTNIS DES ZEHNRINGES [J].
PRELOG, V ;
SCHENKER, K ;
GUNTHARD, HH .
HELVETICA CHIMICA ACTA, 1952, 35 (05) :1598-1615
[25]  
REGITZ M, 1978, CHEM DIAZONIUM DIAZO, P659
[26]   DIE SYNTHESE VON ACETYLEN-CARBONYL-VERBINDUNGEN DURCH FRAGMENTIERUNG VON ALPHA BETA-EPOXY-KETONEN MIT P-TOLUOLSULFONYLHYDRAZIN [J].
SCHREIBE.J ;
FELIX, D ;
ESCHENMO.A ;
WINTER, M ;
GAUTSCHI, F ;
SCHULTEE.KH ;
SUNDT, E ;
OHLOFF, G ;
KALVODA, J ;
KAUFMANN, H ;
WIELAND, P ;
ANNER, G .
HELVETICA CHIMICA ACTA, 1967, 50 (07) :2101-&
[27]  
Theron F., 1978, CHEM CARBON CARBON 1, P381
[28]  
TSUJI J, 1973, TETRAHEDRON LETT, P1573
[29]  
WARNHOFF EW, 1983, J ORG CHEM, V48, P2590
[30]  
WOVKULICH PM, 1991, COMPREHENSIVE ORGANI, V1, P843