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


Moorhoff, CM and Winkler, D, Transformation of substituted 2H-pyran-5-carboxylates into 3R*-vinyl-1,2R*-cyclopropanedicarboxylates, New Journal of Chemistry, 22, (12) pp. 1485-1492. ISSN 1144-0546 (1998) [Refereed Article]

DOI: doi:10.1039/a804237c


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.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Organic chemical synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Moorhoff, CM (Dr Moorhoff)
ID Code:14135
Year Published:1998
Web of Science® Times Cited:6
Deposited By:Chemistry
Deposited On:1998-08-01
Last Modified:2011-08-09

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