Synthesis and fluorine NMR chemical shifts for a series of exo-3,3-difluorotricyclo[3.2.1.02,4]octyl derivatives -: The Diels-Alder alternative to difluorocarbene additions

被引：14

作者：

Battiste, MA ^{[1
]}

Posey, RG ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2000年 / 102卷 / 1-2期

基金：

美国国家科学基金会;

关键词：

F-19 NMR chemical shifts; H-1 NMR chemical shifts; cycloaddition; stereochemistry;

D O I：

10.1016/S0022-1139(99)00290-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The Diels-Alder cycloaddition of 1,2-dihalo-3,3-difluorocyclopropenes 1 to a series of five-membered ring dienes stereoselectively provided the corresponding exo-2,4-dihalo-3,3-difluorotricyclo[3.2.1.0(2,4)]oct-6-ene adducts. Removal of the C2, C4 halogens(bromine or chlorine) before or after saturation of the C6, C7 double bond afforded a variety of gem-difluorocyclopropyl derivatives in the analogous tricyclic manifold. The F-19 and H-1 NMR chemical shifts and coupling constants are listed for each of these tricyclic systems. (C) 2000 Elsevier Science S.A. All rights reserved.

引用

页码：285 / 292

页数：8

共 10 条

[1]

CLOSS GL, 1966, ADV ALICYCLIC CHEM, V1, pCH2

[2]

HALTON B, 1987, CHEM CYCLOPROPYL GRO, pCH32

[3]

JEFFORD CW, 1975, TETRAHEDRON LETT, P823

[4] DIELS-ALDER REACTION OF FURAN AND 2-METHYLFURAN WITH ACRYLONITRILE [J].