On the preparation and unusual reactivity of a potential difluorodienophile

被引：36

作者：

Crowley, PJ

Percy, JM

Stansfield, K

机构：

[1] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND

[2] ZENECA AGROCHEM,JEALOTTS HILL RES STN,BRACKNELL RG12 6EY,BERKS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 45期

关键词：

D O I：

10.1016/0040-4039(96)01876-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Attempts to generate a difluorovinyl sulfone and to react it with cyclopentadiene were hindered by the formation of hydrofluorination products. An alpha-carbamoyloxy-beta,beta-difluoroethenyl phenyl sulfone has been prepared in high yield, but reactions with cyclopentadiene have given predominantly mono-fluorinated cycloadducts, via reduction of the difluorinated compound in situ. Copyright (C) 1996 Elsevier Science Ltd.

引用

收藏

页码：8233 / 8236

页数：4

相关论文

共 14 条

[1] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].

ADAM, W ;

BIALAS, J ;

HADJIARAPOGLOU, L .

CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377

[2]

BARTLETT PD, 1970, QUART REV CHEM SOC, V24, P473

[3] SYNTHESIS OF 2,2,2-TRIFLUOROETHANESULFONIC ACID [J].

BUNYAGIDJ, C ;

PIOTROWSKA, H ;

ALDRIDGE, MH .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16) :3335-3336

[4] DIENOPHILIC PROPERTIES OF PHENYL VINYL SULFONE AND TRANS-1-(PHENYLSULFONYL)-2-(TRIMETHYLSILYL)ETHYLENE - THEIR UTILIZATION AS SYNTHONS FOR ETHYLENE, 1-ALKENES, ACETYLENE, AND MONOSUBSTITUTED ALKYNES IN THE CONSTRUCTION OF FUNCTIONALIZED 6-MEMBERED RINGS VIA [4 + 2] PI-CYCLOADDITION METHODOLOGY [J].

CARR, RVC ;

WILLIAMS, RV ;

PAQUETTE, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :4976-4986

[5] CAPTODATIVE SUBSTITUENT EFFECTS .31. OLEFINS WITH CAPTODATIVE SUBSTITUTION IN [2+2] CYCLO-ADDITIONS [J].

DECOCK, C ;

PIETTRE, S ;

LAHOUSSE, F ;

JANOUSEK, Z ;

MERENYI, R ;

VIEHE, HG .

TETRAHEDRON, 1985, 41 (19) :4183-4193

[6] NEW FLUORINE-CONTAINING BUILDING-BLOCKS FROM TRIFLUOROETHANOL .2. [J].

HOWARTH, JA ;

OWTON, WM ;

PERCY, JM ;

ROCK, MH .

TETRAHEDRON, 1995, 51 (37) :10289-10302

[7]

KOTSUKI H, 1983, TETRAHEDRON LETT, V32, P4155

[8]

LEORY J, 1987, J ORG CHEM, V52, P290

[9] SODIUM PERBORATE - A CHEAP AND EFFECTIVE REAGENT FOR THE OXIDATION OF ANILINES AND SULFIDES [J].

MCKILLOP, A ;

TARBIN, JA .

TETRAHEDRON LETTERS, 1983, 24 (14) :1505-1508

[10] APPLICATIONS OF ORGANOFLUORINE REAGENTS IN GENERAL ORGANIC-SYNTHESIS .9. - SYNTHETIC UTILITY OF A FLUORINE-FACILITATED CLAISEN REARRANGEMENT - A NOVEL SYNTHETIC METHOD FOR 2,4-ALKADIENOIC ACIDS USING 2,2,2-TRIFLUOROETHYL PHENYL SULFOXIDE [J].

NAKAI, T ;

TANAKA, K ;

OGASAWARA, K ;

ISHIKAWA, N .

CHEMISTRY LETTERS, 1981, (09) :1289-1292