TY - JOUR
T1 - Transformation of substituted 2H-pyran-5-carboxylates into 3R*-vinyl-1,2R*-cyclopropanedicarboxylates
AU - Moorhoff, Cornelis M.
AU - Winkler, Dave
PY - 1998/12
Y1 - 1998/12
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0009625066&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0009625066
SN - 1144-0546
VL - 22
SP - 1485
EP - 1492
JO - New Journal of Chemistry
JF - New Journal of Chemistry
IS - 12
ER -