Transformation of substituted 2H-pyran-5-carboxylates into 3R*-vinyl-1,2R*-cyclopropanedicarboxylates

Cornelis M. Moorhoff, Dave Winkler

Research output: Contribution to journalArticleOther

3 Citations (Scopus)


Substituted alkyl 2H-pyran-5-carboxylates, 1, have been condensed with methyl 2-(triphenylarsoranylidene) ethanoate, 14a, to form substituted 3-vinyl-1,2-cyclopropanedicarboxylates, 15, and, in a number of cases, 2,3-dihydro-3-vinyl-2,4-furandicarboxylates, 16. NMR experiments showed that for the majority of cyclopropane products formed, the cyclopropane ring hydrogen atoms have the trans configuration. This was validated by molecular orbital calculations. Biological screening tests revealed that these compounds showed some ectoparasiticidal activity.

Original languageEnglish
Pages (from-to)1485-1492
Number of pages8
JournalNew Journal of Chemistry
Issue number12
Publication statusPublished - Dec 1998
Externally publishedYes

Cite this