Stereochemistry and kinetics of amines addition to acetylenic esters
- 1 September 1991
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 69 (9) , 1445-1449
- https://doi.org/10.1139/v91-213
Abstract
The reactions of a series of methyl para-substituted phenylpropiolates 1a–e with piperidine, morpholine, and diethylamine in methanol and dimethylformamide (DMF) have been studied and their rates measured. The products were methyl β-(N,N-dialkylamino)-p-substituted cinnamates 2–4a–e. 1H NMR spectra were used to determine the configuration of the products. The ρ values in methanol ranged between 0.34 and 1.24 whereas in DMF they were between 0.85 and 1.88. The values of ΔS≠ favor a bimolecular rate-limiting step mechanism. Key words: nucleophilic addition to acetylenic esters.Keywords
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