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Synthesis of stable derivatives of cycloprop-2-ene carboxylic acid.

ABSTRACT: Large-scale syntheses of 3-(cycloprop-2-en-1-oyl)oxazolidinones from acetylene and ethyl diazoacetate are described. Unlike other cyclopropenes that bear a single substitutent at C-3, these compounds are stable to long-term storage. Although the cyclopropene derivatives are unusually stable, they are reactive toward cyclic and acyclic dienes in stereoselective Diels-Alder reactions.

SUBMITTER: Yan N

PROVIDER: S-EPMC3132478 | biostudies-literature | 2008 Jun

REPOSITORIES: biostudies-literature

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Synthesis of stable derivatives of cycloprop-2-ene carboxylic acid.

Yan Ni N Liu Xiaozhong X Pallerla Mahesh K MK Fox Joseph M JM

The Journal of organic chemistry 20080502 11

Large-scale syntheses of 3-(cycloprop-2-en-1-oyl)oxazolidinones from acetylene and ethyl diazoacetate are described. Unlike other cyclopropenes that bear a single substitutent at C-3, these compounds are stable to long-term storage. Although the cyclopropene derivatives are unusually stable, they are reactive toward cyclic and acyclic dienes in stereoselective Diels-Alder reactions. ...[more]

PMID: 18452335

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