PYRAZOLINES: IV. REARRANGEMENT OF ALKYL GROUPS DURING THE PYROLYSIS OF 4,4-DIALKYL-3-CYANO-3-CARBOMETHOXY-Δ1-PYRAZOLINES
- 1 May 1965
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 43 (5) , 1389-1397
- https://doi.org/10.1139/v65-188
Abstract
A number of 4,4-dialkyl-3-cyano-3-carbomethoxy-Δ1-pyrazolines have been synthesized. Pyrolysis of these pyrazolines yielded cyclopropane and olefin products. The formation of olefin products by rearrangement of an alkyl group from C4 to C5 of the pyrazoline system suggests that positive charge is developed on C5 in the transition state. Ionic character in the transition state was also indicated by the fact that the rate of pyrolysis is faster in polar than in nonpolar solvents.Keywords
This publication has 6 references indexed in Scilit:
- Nuclear Magnetic Resonance Spectroscopy. Cyclopropane DerivativesJournal of the American Chemical Society, 1963
- Stereochemistry of the Formation and Decomposition of 1-PyrazolinesJournal of the American Chemical Society, 1962
- N.M.R. SPECTRA OF SOME α–β UNSATURATED ESTERSCanadian Journal of Chemistry, 1961
- The Reaction of Ketones with DiazomethaneJournal of the American Chemical Society, 1960
- Some New Phenothiazine Derivatives of Pharmacological Interest.Acta Chemica Scandinavica, 1949
- Condensation Reactions. I. The Condensation of Ketones with Cyanoacetic Esters and the Mechanism of the Knoevenagel ReactionJournal of the American Chemical Society, 1937