A NEW SYNTHESIS OF 2-FLUORO-1-OLEFINS

被引：44

作者：

MCCARTHY, JR

MATTHEWS, DP

BARNEY, CL

机构：

[1] Merrell Dow Research Institute, Cincinnati, OH 45215

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(00)94406-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first examples of the addition of PhSeF to olefins to yield β-fluoro phenylselenides (2) are reported. β-Fluoro phenylselenides (2) obtained from terminal olefins were converted to the title vinyl fluorides 3 on treatment with ozone, whereas, 2 obtained from internal and cyclic olefins formed allyl fluorides. This method provides an entry to previously unreported 2-benzyl-2-fluoro-1-olefins (e.g. 3i). © 1990.

引用

页码：973 / 976

页数：4

共 33 条

[1] HIGHLY EFFECTIVE MECHANISM-BASED INACTIVATION OF DOPAMINE BETA-HYDROXYLASE BY A NOVEL KETENE THIOACETAL
BARGAR, TM
BROERSMA, RJ
CREEMER, LC
MCCARTHY, JR
HORNSPERGER, JM
ATTWOOD, PV
JUNG, MJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) : 2975 - 2976
[2] SYNTHESES OF ORGANOFLUORINE COMPOUNDS .8. SOLVOLYTIC RING-OPENING OF ALKOXYCHLOROFLUOROCYCLOPROPANES - READY ACCESS TO FLUORINATED ALPHA-BETA-UNSATURATED ALDEHYDES AND KETONES
BESSIERE, Y
SAVARY, DNH
SCHLOSSER, M
[J]. HELVETICA CHIMICA ACTA, 1977, 60 (05) : 1739 - 1746
[3] (E)-2-(3,4-DIMETHOXYPHENYL)-3-FLUOROALLYLAMINE - A SELECTIVE, ENZYME-ACTIVATED INHIBITOR OF TYPE-B MONOAMINE-OXIDASE
BEY, P
FOZARD, J
LACOSTE, JM
MCDONALD, IA
ZREIKA, M
PALFREYMAN, MG
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (01) : 9 - 10
[4] STEREOSPECIFIC PREPARATION OF (Z)-ISOMERS AND (E)-ISOMERS, RESPECTIVELY, OF SOME VINYL FLUORIDES
BOCHE, G
FAHRMANN, U
[J]. CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (12): : 4005 - 4009
[5] BROERSMA RJ, UNPUB
[6] BUDDRUS J, 1966, TETRAHEDRON LETT, P5379
[7] FLUORO OLEFINS .7. PREPARATION OF TERMINAL VINYL FLUORIDES
BURTON, DJ
GREENLIMB, PE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (19) : 2796 - 2801
[8] SYNTHESIS OF A CYTOTOXIC VERNOLEPIN PROTOTYPE - OZONIZATION OF SILYLOXYALKENES
CLARK, RD
HEATHCOCK, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) : 1396 - 1403
[9] PHENYLSELENIUM TRICHLORIDE IN ORGANIC-SYNTHESIS - REACTION WITH UNSATURATED-COMPOUNDS - PREPARATION OF VINYLIC CHLORIDES VIA SELENOXIDE ELIMINATION
ENGMAN, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) : 4086 - 4094
[10] HANACK M, 1978, SYNTHESIS-STUTTGART, P217

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