Facile dibromoolefination of lactones using bromomethylenetriphenylphosphorane

被引：14

作者：

Lakhrissi, Y ^{[1
]}

Taillefumier, C ^{[1
]}

Chrétien, F ^{[1
]}

Chapleur, Y ^{[1
]}

机构：

[1] Univ Nancy 1, CNRS, Grp SUCRES, Unite Mixte Rech, F-54506 Vandoeuvre Les Nancy, France

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(01)01531-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dibromoolefination of lactones was achieved in high yields using bromomethylenetriphenylphosphorane in refluxing tetrahydrofuran. This reaction is believed to proceed via bromination of the monobromophosphorane from the corresponding bromomethyltriphenylphosphonium bromide with concomitant formation of methylenetriphenylphosphorane as shown by P-31 NMR. Transylidation should Occur to afford the reactive dibromomethylenetriphenylphosphorane. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7265 / 7268

页数：4

共 29 条

[1] GENERAL REACTION OF PHOSPHINES AND CARBON-TETRACHLORIDE ON NUCLEOPHILES .29. REACTIONS IN SYSTEM TRIPHENYLPHOSPHINE-CARBON TETRACHLORIDE
APPEL, R
KNOLL, F
MICHEL, W
MORBACH, W
WIHLER, HD
VELTMANN, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (01): : 58 - 70
[2] TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE
APPEL, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12): : 801 - 811
[3] Suzuki arylation of 1,1-dibromo-1-alkenes: Synthesis of tetra-substituted alkenes
Bauer, A
Miller, MW
Vice, SF
McCombie, SW
[J]. SYNLETT, 2001, (02) : 254 - 256
[4] Bestmann H. J., 1991, COMPREHENSIVE ORGANI, V6, P171
[5] FORMATION OF Z-1-VINYLIODIDES VIA THE WITTIG REACTION
BESTMANN, HJ
RIPPEL, HC
DOSTALEK, R
[J]. TETRAHEDRON LETTERS, 1989, 30 (39) : 5261 - 5262
[6] REAKTIONEN MIT PHOSPHIN-ALKYLENEN .1. INTERMOLEKULARE UMYLIDIERUNG ZWISCHEN PHOSPHONIUMSALZEN UND PHOSPHIN-ALKYLENEN
BESTMANN, HJ
[J]. CHEMISCHE BERICHTE-RECUEIL, 1962, 95 (01): : 58 - &
[7] COREY EJ, 1972, TETRAHEDRON LETT, P3769
[8] C-GLYCOSIDES .9. STEREOSPECIFIC SYNTHESIS OF C-GLYCOSIDIC SPIROKETAL OF THE PAPULACANDINS
CZERNECKI, S
PERLAT, MC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) : 6289 - 6292
[9] Eymery F, 2000, SYNTHESIS-STUTTGART, P185
[10] STABILE PHOSPHIN-YLIDE - ZUR FRAGE DER DPI-PPI-WECHSELWIRKUNG
FISCHER, H
FISCHER, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (02): : 658 - &

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