Synthesis of stable derivatives of cycloprop-2-ene carboxylic acid.
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.
Yan
Ni
N
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA.
Liu
Xiaozhong
X
Pallerla
Mahesh K
MK
Fox
Joseph M
JM
D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
D002264:Carboxylic Acids; D003521:Cyclopropanes; C021985:cyclopropene