REACTION OF 2,2-DIFLUOROVINYL KETONES WITH HETEROATOM NUCLEOPHILES - A GENERAL ONE-POT SYNTHESIS OF ALPHA-OXOKETENE ACETALS

被引:45
作者
ICHIKAWA, J
KOBAYASHI, M
YOKOTA, N
NODA, Y
MINAMI, T
机构
[1] Department of Applied Chemistry, Kyushu Institute of Technology, Kitakyushu, 804, Sensui-cho, Tobata
关键词
D O I
10.1016/S0040-4020(01)85658-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,2-Difluorovinyl ketones readily react with heteroatom nucleophiles such as thiols, alcohols, and amines to undergo stepwise replacement of the two fluorine atoms via addition-elimination process. The reaction affords alpha-oxoketene acetals including S,S-, N,S-, N,N-, O,S-, and O,O-acetals in good to excellent yields.
引用
收藏
页码:11637 / 11646
页数:10
相关论文
共 27 条
[1]  
ASOKAN CV, 1985, SYNTHESIS-STUTTGART, P163
[2]   STUDIES ON CYCLOADDITION REACTIONS OF 1,3-DIPHENYL-2-AZAALLYL LITHIUM AND ETHYL(BENZYLIDENEAMINO)ACETATE ANION WITH ALPHA-OXOKETENE DITHIOACETALS [J].
BALU, MP ;
ILA, H ;
JUNJAPPA, H .
TETRAHEDRON, 1990, 46 (19) :6771-6782
[3]   REACTIONS OF KETEN ACETALS .7. TOTAL SYNTHESES OF TETRAMETHYL ETHERS OF 1-ACYL-2,4,5,7-TETRAHYDROXYANTHRAQUINONES RHODOLAMPROMETRIN AND RHODOCOMATULIN [J].
BANVILLE, J ;
BRASSARD, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (17) :1852-1856
[4]   ATTEMPTED SIMMONS-SMITH REACTION ON ALPHA-OXOKETENE DITHIOACETALS - A NEW GENERAL-ROUTE TO 3,4-SUBSTITUTED AND ANNELATED THIOPHENES [J].
BHAT, L ;
THOMAS, A ;
ILA, H ;
JUNJAPPA, H .
TETRAHEDRON, 1992, 48 (47) :10377-10388
[5]   A NOVEL INTRAMOLECULAR ESTER ENOLATE ALKYLATION - PREPARATION OF ACYLKETENE ACETALS [J].
BROADHURST, MD .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07) :1117-1118
[6]   OXOKETENE DITHIOACETALS AS VERSATILE SYNTHONS FOR ALTERNATIVE 1,3 TO 1,11 CARBONYL TRANSPOSITIONS - A NEW POLYENE SYNTHESIS [J].
CHANDRASEKHARAM, M ;
ASOKAN, CV ;
ILA, H ;
JUNJAPPA, H .
TETRAHEDRON LETTERS, 1990, 31 (12) :1763-1766
[7]   REFORMATSKY REACTION ON ALPHA-OXO KETENE DITHIOACETALS - SYNTHESIS OF SUBSTITUTED AND FUSED ETHYL 2-HYDROXY-6-(METHYLTHIO)BENZOATES, 6-(METHYLTHIO)PYRAN-2-ONES, AND 6-(METHYLTHIO)-2(1H)-PYRIDONE DERIVATIVES [J].
DATTA, A ;
ILA, H ;
JUNJAPPA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5589-5594
[8]   ALPHA-OXO KETENE DITHIOACETALS AND RELATED-COMPOUNDS - VERSATILE 3-CARBON SYNTHONS [J].
DIETER, RK .
TETRAHEDRON, 1986, 42 (12) :3029-3096
[9]   ENANTIOMERICALLY PURE KETALS IN SYNTHESIS - DIASTEREOSELECTIVE FORMATION OF BETA-KETO AND BETA-HYDROXY KETALS [J].
EID, CN ;
KONOPELSKI, JP .
TETRAHEDRON LETTERS, 1991, 32 (04) :461-464
[10]   ACYLKETENE ACETALS IN ORGANIC-SYNTHESIS [J].
EID, CN ;
KONOPELSKI, JP .
TETRAHEDRON, 1991, 47 (06) :975-992