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The Synthesis and Polymerization of 1,3-Disubstituted Cyclohexanes. II. cis-1,3-Diformylcyclohexane and cis-1,3-Divinylcyclohexane

 

作者: G.C. Corfield,   A. Crawshaw,  

 

期刊: Journal of Macromolecular Science: Part A - Chemistry  (Taylor Available online 1971)
卷期: Volume 5, issue 1  

页码: 21-35

 

ISSN:0022-233X

 

年代: 1971

 

DOI:10.1080/00222337108061023

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

The synthesis of cis-1,3-diformylcyclohexane by a hydride reduction of the dimethyl ester of cyclohexane-cis-1,3-dicarboxylic acid is described. An inversion of configuration occurred during an attempt to prepare trans-l,3-diformylcyclohexane by a similar route, cis-1,3-Divinylcyclohexane was prepared by a Wittig reaction on the corresponding dialdehyde. Polymerization of cis-1,3-diformylcyclohexane using a cationic catalyst gave high yields of thermally unstable polymers. Soluble fractions of the polymers contained some residual aldehyde groups. Spectroscopic data confirmed that these polymers contained 3-oxabicyclo[3,3,1] nonane rings formed through a cyclopolymerization mechanism. Polymerization of cis-1,3-divinylcyclohexane using a Ziegler catalyst resulted in soluble polymers containing little residual unsaturation. This soluble polymer, from the evidence, is a cyclopolymer containing bicyclo[3,3,1] nonane units.

 

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