Synthesis of Perfluoroalkyl-Substituted Vinylcyclopropanes by Way of Enhanced Neighboring Group Participation

被引：18

作者：

Kelly, Christopher B. ^{[1
]}

Mercadante, Michael A. ^{[1
]}

Carnaghan, Emma R. ^{[1
]}

Doherty, Matthew J. ^{[2
]}

Fager, Diana C. ^{[2
]}

Hauck, John J. ^{[2
]}

MacInnis, Allyson E. ^{[2
]}

Tilley, Leon J. ^{[2
]}

Leadbeater, Nicholas E. ^{[1
,3
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

[2] Stonehill Coll, Dept Chem, Easton, MA 02357 USA

[3] Univ Connecticut, Ctr Hlth, Dept Community Med & Hlth Care, Exchange, Farmington, CT 06030 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 19期

基金：

美国国家科学基金会;

关键词：

Synthetic methods; Fluorine; Organofluorine compounds; Organosilicon compounds; Cyclopropanes; Carbocations; FLUORINE; SOLVOLYSIS; C4H7+; IONS; CYCLOPROPYLCARBINYL; GENERATION; ENERGIES; CATION; MODES;

D O I：

10.1002/ejoc.201500565

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, high yielding, two-step, one-pot protocol for the preparation of trifluoromethyl-substituted vinylcyclopropanes from -CF3 homoallyl alcohols is disclosed. Destabilization of the cationic intermediate by the electron-withdrawing CF3 group greatly enhances neighboring group participation of the alkene, allowing ring closure to predominate. The reaction can be extended to the difluoromethyl and pentafluoroethyl group, enabling the preparation of a diverse array of fluoroalkyl-substituted vinylcyclopropanes.

引用

页码：4071 / 4076

页数：6

共 50 条

[21] STEREOSELECTIVE SYNTHESIS OF A CONDENSED TANNIN USING NEIGHBORING GROUP PARTICIPATION
KAWAMOTO, H
TANAKA, N
NAKATSUBO, F
MURAKAMI, K
MOKUZAI GAKKAISHI, 1993, 39 (07): : 820 - 824
[22] SYNTHESIS, STRUCTURE-PROPERTY RELATIONS AND LYOTROPIC BEHAVIOR OF PERFLUOROALKYL-SUBSTITUTED PARA-LINKED AROMATIC POLYAMIDES
HATKE, W
SCHMIDT, HW
MACROMOLECULAR CHEMISTRY AND PHYSICS, 1994, 195 (11) : 3579 - 3595
[23] PARTICIPATION OF A NEIGHBORING AMIDE GROUP IN DECOMPOSITION OF ESTERS AND AMIDES OF SUBSTITUTED PHTHALAMIC ACIDS
SHAFER, JA
MORAWETZ, H
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (07): : 1899 - &
[24] The Influence of Neighboring Group Participation on the Hydrolysis of 2-O-Substituted Methyl Glucopyranosides
Heuckendorff, Mads
Pedersen, Christian M.
Bols, Mikael
ORGANIC LETTERS, 2011, 13 (22) : 5956 - 5959
[25] Benzothiazines in organic synthesis: formation of a cyclopropane via neighboring group participation
Cai, Zhengxin
Harmata, Michael
TETRAHEDRON LETTERS, 2013, 54 (08) : 814 - 816
[26] NEIGHBORING GROUP PARTICIPATION IN CONVERSION OF BETA-SUBSTITUTED ETHANESULFONATE SALTS TO BETA-SUBSTITUTED ETHANESULFONYL CHLORIDES
MCMANUS, SP
SMITH, MR
HERRMANN, FT
ABRAMOVITCH, RA
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (04): : 647 - 649
[27] A NOVEL STRATEGY FOR THE PREPARATION OF SUBSTITUTED TETRAHYDROFURANS BASED ON NEIGHBORING GROUP PARTICIPATION BY THE RING OXYGEN OF MONOSACCHARIDES
WILSON, P
SHAN, WF
MOOTOO, DR
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1994, 13 (01) : 133 - 140
[28] NEIGHBORING GROUP PARTICIPATION IN PUMMERER-TYPE REARRANGEMENTS OF ORTHO-SUBSTITUTED ARYLMETHYL SULFOXIDES
FINDLAY, JBC
FISHWICK, CWG
KERSEY, ID
WARD, P
TETRAHEDRON LETTERS, 1995, 36 (13) : 2299 - 2302
[29] NEIGHBORING GROUP PARTICIPATION BY OXYGEN IN THE SOLVOLYSIS OF ACYCLIC GAMMA-ALKOXY SUBSTITUTED PARA-TOLUENESULFONATES
ELIEL, EL
CLAWSON, L
KNOX, DE
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (15): : 2707 - 2711
[30] CONFORMATIONAL AND STEREOCHEMICAL CONTROL OF AN UNPRECEDENTED NEIGHBORING GROUP PARTICIPATION - NEW, STEREOSPECIFIC CHLOROEPOXIDE SYNTHESIS
GANEM, B
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (03) : 858 - 859

← 1 2 3 4 5 →