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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