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Novel Conversions of a Multifunctional, Bio-sourced Lactone Carboxylic Acid.

ABSTRACT: The plant-derived compounds furfuryl alcohol and itaconic anhydride are known to undergo a Diels-Alder reaction at room temperature and in bulk to efficiently give an alkene-containing lactone carboxylic acid. Reported here is the conversion of this substance to a variety of derivatives via hydrogenation, epoxidation, or halolactonization reactions. Most notable is the formation of a set of three related acrylate or methacrylate esters (see graphical abstract) produced by direct acylative ring opening of ether bonds using Sc(OTf)₃ and (meth)acrylic anhydride. These esters are viewed as promising candidates for use as biorenewable monomers in reversible addition-fragmentation chain transfer (RAFT) polymerization reactions.

SUBMITTER: Kaicharla T

PROVIDER: S-EPMC10869105 | biostudies-literature | 2024

REPOSITORIES: biostudies-literature

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Novel Conversions of a Multifunctional, Bio-sourced Lactone Carboxylic Acid.

Kaicharla Trinadh T Lee Sangjun S Wang Ruiqin R Pehere Ashok D AD Xu Shu S Hoye Thomas R TR

ARKIVOC : free online journal of organic chemistry 20231210

The plant-derived compounds furfuryl alcohol and itaconic anhydride are known to undergo a Diels-Alder reaction at room temperature and in bulk to efficiently give an alkene-containing lactone carboxylic acid. Reported here is the conversion of this substance to a variety of derivatives via hydrogenation, epoxidation, or halolactonization reactions. Most notable is the formation of a set of three related acrylate or methacrylate esters (see graphical abstract) produced by direct acylative ring o ...[more]

PMID: 38361761

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