PREPARATION OF ALPHA,BETA-UNSATURATED METHYL KETONES FROM DIKETENE USING BIS(TRIBUTYLTIN) OXIDE

被引:13
作者
SHIBATA, I
NISHIO, M
BABA, A
MATSUDA, H
机构
关键词
D O I
10.1246/cl.1993.1219
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel type tin enolate is easily formed by the regioselective ring cleavage of diketene with Bis(tributyltin) oxide [(n-Bu3Sn)2O]. The enolate caused carbon-carbon bond formation with aldehydes. As a result, alpha,beta-unsaturated methyl ketones were obtained in good yields, accompanied by decarboxylation.
引用
收藏
页码:1219 / 1222
页数:4
相关论文
共 12 条
[1]   CHANGE OF REGIOSELECTIVITY IN THE REACTION OF TIN ENOLATES AND ALPHA-BROMO KETONES - SYNTHESIS OF 1,4-DIKETONES UNDER NONRADICAL CONDITIONS [J].
BABA, A ;
YASUDA, M ;
YANO, K ;
SHIBATA, I ;
MATSUDA, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3205-3207
[2]   DIKETENE [J].
CLEMENS, RJ .
CHEMICAL REVIEWS, 1986, 86 (02) :241-318
[3]   REACTIONS OF GROUP 4 ORGANOMETALLIC COMPOUNDS .6. REACTION BETWEEN TRIMETHYLTIN METHOXIDE AND BETA-PROPIOLACTONE [J].
ITOH, K ;
KOBAYASH.S ;
SAKAI, S ;
ISHII, Y .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 10 (03) :451-&
[4]  
PEREYRE M, 1967, B SOC CHIM FR, P1928
[5]   ACTION OF TRIORGANOTIN ALKALOIDS ON ENOL ESTERS - PROBLEM OF OBTAINING C-OR O-STANNYLATED COMPOUNDS [J].
PEREYRE, M ;
BELLEGAR.B ;
MENDELSO.J ;
VALADE, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1968, 11 (01) :97-&
[6]  
PEREYRE M, 1987, TIN ORGANIC SYNTHESI, P286
[7]   TOTAL SYNTHESIS OF ENTEROBACTIN VIA AN ORGANOTIN TEMPLATE [J].
SHANZER, A ;
LIBMAN, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (15) :846-847
[8]   SYNTHESIS OF HYDROXY LACTONES BY BIS(TRIBUTYLTIN) OXIDE PROMOTED RING EXPANSION OF HALO LACTONES [J].
SHIBATA, I ;
MATSUO, F ;
BABA, A ;
MATSUDA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :475-476
[9]   SYNTHESIS OF HETEROCYCLIC-COMPOUNDS BY THE ORGANOTIN ALKOXIDE PROMOTED CLEAVAGE OF GAMMA-BROMO BETA-LACTONES [J].
SHIBATA, I ;
TOYOTA, M ;
BABA, A ;
MATSUDA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2487-2491
[10]  
SHIBATA I, 1992, CHEM EXPRESS, V7, P49