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Stereochemistry and kinetics of addition of amines to acetylenic ketones
Author(s) -
Hamed Ezzat A.,
Sharaf Saber M.,
AbdelBaky Samy A.,
Ibrahim Mahmoud F.,
Youssef AbdelHamid A.
Publication year - 1990
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610031002
Subject(s) - morpholine , piperidine , chemistry , nucleophile , kinetics , methanol , stereochemistry , proton nmr , medicinal chemistry , organic chemistry , catalysis , physics , quantum mechanics
The reactions of a series of 3‐( p ‐substituted phenyl)‐1‐phenylprop‐2‐yn‐1‐ones with piperidine and morpholine in methanol were studied and their rates measured. The products were 3‐piperidino‐ and 3‐morpholino‐3‐( p ‐substituted phenyl)‐1‐phenylprop‐2‐en‐1‐ones. 1 H NMR spectra were used to determine the configurations of the obtained products. A good Hammett correlation was obtained with ρ values of 1·15–1·10 and 1·15–0·53 for piperidine and morpholine, respectively, which suggest a carbanionic character of the transition state. A two‐step mechanism is postulated for these nucleophilic additions.