Isobenzofuran (IBF) precursor characterization using IR, NMR, X-ray and thermogravimetric analysis

被引：3
|
作者：
Packe-Wirth, R
Enkelmann, V
机构：
[1] Master Builders, Cleveland, OH 44122 USA
[2] Max Planck Inst Polymerforsch, D-55128 Mainz, Germany
来源：
JOURNAL OF MOLECULAR STRUCTURE | 1998年 / 448卷 / 01期
关键词：
characterization; isobenzofuran; cyclopentadienone; stereoisomer;
D O I：
10.1016/S0022-2860(98)00324-X
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The Diels-Alder (DA) addition product of epoxynaphthalene with tetraphenylcyclopentadienone serves as a precursor for isobenzofuran (IBF), one of the most reactive dienes known. A detailed investigation on the DA reaction of epoxynaphthalene with tetraphenylcyclopentadienone shows, that in addition to the main, commonly described DA product [Fieser and Haddadin, J. Am. Chem Sec. 86 (1964) 2081;Fieser and Haddadin, Can. J. Chem. 43 (1965) 1599], another stereoisomer by-product is formed. The two isomers are compared with respect to their thermal and spectroscopic properties. Spectroscopic investigations show that Fieser's assumed exo,exo-configuration for the main product is indead an exo,endo-configuration. The by-product turns out to be the exo,exo-stereoisomer. (C) 1998 Elsevier Science B.V. All rights reserved.
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页码：1 / 9
页数：9
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