Incorporation of hexafluorobutyne into furans or phenols via reaction with iron(0) carbene or vinylketene complexes

被引：9

作者：

Akhani, Ravish K. ^{[1
]}

Atiq-ur-Rehman ^{[2
]}

Schnatter, Wayne F. K. ^{[1
]}

机构：

[1] Long Isl Univ, Dept Chem & Biochem, Brooklyn, NY 11201 USA

[2] CanAm Biores Inc, Winnipeg, MB R3T 0P4, Canada

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 08期

关键词：

TRANSITION-METAL-COMPLEXES; (2-FURYL)CARBENE COMPLEXES; CYCLOADDITION REACTIONS; PRODUCT DISTRIBUTION; ALKYNES; DERIVATIVES; CHROMIUM; SKELETON; LIGANDS;

D O I：

10.1016/j.tetlet.2008.12.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of iron(0) carbene complexes with hexafluorobut-2-yne produces 3,4-bis(trifluoromethylated)furans in a process that is favored for electron-rich carbenes. No traces of furannulation or benzannulation are observed with Group 6 Fischer carbenes. Reaction of hexafluorobut-2-yne with a vinylketene iron(0) complex gives a 2,3-bis-trifluoromethylated phenol. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：930 / 932

页数：3

共 41 条

[1] REACTION OF 2-LITHIO-3.4-BIS(TRIFLUOROMETHYL)FURAN WITH ELECTROPHILES
ABUBAKAR, AB
BOOTH, BL
TIPPING, AE
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1991, 55 (02) : 189 - 198
[2] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .36. MONOFUNCTIONAL TRI(METHYLENE)METHANE CHROMIUM AND IRON COMPLEXES BY ADDITION OF ALLENES TO M = C BONDS OF CARBENE COMPLEXES
AUMANN, R
TRENTMANN, B
[J]. CHEMISCHE BERICHTE-RECUEIL, 1989, 122 (10): : 1977 - 1982
[3] Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes
Barluenga, Jose
Riesgo, Lorena
Vicente, Ruben
Lopez, Luis A.
Tomas, Miguel
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) : 13528 - +
[4] REACTIONS INVOLVING FLUORIDE-ION .39. REACTIONS OF PERFLUORINATED DIENES WITH OXYGEN AND SULFUR NUCLEOPHILES
BRISCOE, MW
CHAMBERS, RD
MULLINS, SJ
NAKAMURA, T
VAUGHAN, JFS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (21): : 3119 - 3124
[5] HEXA(TRIFLUOROMETHYL)BENZENE
BROWN, HC
GEWANTER, HL
WHITE, DM
WOODS, WG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (04) : 634 - 635
[6] REACTION OF HEXAFLUOROBUT-2-YNE WITH CARBONYL COMPLEXES OF IRON, RUTHENIUM, AND OSMIUM
BURT, R
COOKE, M
GREEN, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1970, (18): : 2981 - &
[7] Furan forming reactions of cis-2-alken-4-yn-1-ones
Casey, CP
Strotman, NA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) : 2576 - 2581
[8] Equilibrium between η2-(o-ethynylbenzoyl)rhenium complexes and rhenium isobenzofuryl carbene complexes and subsequent reactions of isobenzofuryl carbene complexes
Casey, CP
Strotman, NA
Guzei, IA
[J]. ORGANOMETALLICS, 2004, 23 (17) : 4121 - 4130
[9] Polyhalogenated heterocyclic compounds .41. Cycloaddition reactions involving hexafluorobut-2-yne and 1,1,1,2,4,4,4-heptafluorobut-2-ene
Chambers, RD
Roche, AJ
Rock, MH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (11): : 1095 - 1100
[10] The cycloaddition reactions of 2-ethoxy-3-phenylvinylketene iron(0) with alkynes to yield catechol derivatives
Darbasie, ND
Schnatter, WFK
Warner, KF
Manolache, N
[J]. TETRAHEDRON LETTERS, 2006, 47 (06) : 963 - 966

← 1 2 3 4 5 →