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

来源：

TETRAHEDRON | 1994年 / 50卷 / 40期

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

页码：11637 / 11646

页数：10

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
BALU, MP
ILA, H
JUNJAPPA, H
[J]. 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
BANVILLE, J
BRASSARD, P
[J]. 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
BHAT, L
THOMAS, A
ILA, H
JUNJAPPA, H
[J]. TETRAHEDRON, 1992, 48 (47) : 10377 - 10388
[5] A NOVEL INTRAMOLECULAR ESTER ENOLATE ALKYLATION - PREPARATION OF ACYLKETENE ACETALS
BROADHURST, MD
[J]. 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
CHANDRASEKHARAM, M
ASOKAN, CV
ILA, H
JUNJAPPA, H
[J]. 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
DATTA, A
ILA, H
JUNJAPPA, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) : 5589 - 5594
[8] ALPHA-OXO KETENE DITHIOACETALS AND RELATED-COMPOUNDS - VERSATILE 3-CARBON SYNTHONS
DIETER, RK
[J]. TETRAHEDRON, 1986, 42 (12) : 3029 - 3096
[9] ENANTIOMERICALLY PURE KETALS IN SYNTHESIS - DIASTEREOSELECTIVE FORMATION OF BETA-KETO AND BETA-HYDROXY KETALS
EID, CN
KONOPELSKI, JP
[J]. TETRAHEDRON LETTERS, 1991, 32 (04) : 461 - 464
[10] ACYLKETENE ACETALS IN ORGANIC-SYNTHESIS
EID, CN
KONOPELSKI, JP
[J]. TETRAHEDRON, 1991, 47 (06) : 975 - 992

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