HALOALDEHYDE POLYMERS .45. SEPARATION OF FLUOROCHLOROBROMOACETIC ACID INTO ITS ANTIPODES - SYNTHESIS OF OPTICALLY-ACTIVE FLUOROCHLOROBROMOACETALDEHYDE AND ITS POLYMERIZATION

POLYMER

卷:32

Article

DOYLE, TR ; VOGL, O

关键词: HALOALDEHYDE POLYMERS;    FLUOROCHLOROBROMOACETIC ACID;    SYNTHESIS;    POLYMERIZATION;    FLUOROCHLOROBROMOACETALDEHYDE;   

DOI  :  10.1016/0032-3861(91)90491-Z

来源: Elsevier

【 摘 要 】

Racemic fluorochlorobromoacetic acid (FCBAA) was separated into its antipodes by recrystallization of the strychnine salts. Optically active FCBAA with a maximum enantiomeric purity of 66% was obtained. The enantiomeric purity was determined by F-19 nuclear magnetic resonance spectroscopy of the bornyl esters of FCBAA. The (+)-ethyl ester and the (-)-methyl/ethyl ester of FCBAA were reduced with diisobutyl aluminium hydride and, after work-up, gave a mixture of the hydrates and the hemiacetals of (+)- and (-)-fluorochlorobromoacetaldehyde (FCBA), which was dehydrated to optically active FCBA. The optical rotation of (+)- and (-)-FCBA indicated its enantiomeric purity to be similar to that of the parent FCBAA. Optically active FCBA was polymerized and the resulting polymer was characterized.

【 授权许可】

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