Citation:KISSANE, M., MURPHY, M., O'BRIEN, E., CHOPRA, J., MURPHY, L., COLLINS, S. G., LAWRENCE, S. E. & MAGUIRE, A. R., 2011. Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles. Organic & Biomolecular Chemistry, 9, 2452-2472. doi: 10.1039/C0OB00805B
Synthetically versatile conjugate addition of a range of carbon, nitrogen, oxygen, sulfur and selenium nucleophiles to the highly functionalised 2-thio-3-chloroacrylamides is
described. The stereochemical and synthetic features of this transformation are discussed in detail. In most instances, the nucleophile replaces the chloro substituent with retention of stereochemistry. With the oxygen nucleophiles, a second addition can occur leading to
acetals, while with the nitrogen nucleophiles, E-Z isomerism occurs in the resulting enamine derivatives. The ratio of the E/Z isomers can be rationalised on the basis of the substituent and the level of oxidation.
Byrne, Peter A.; Karaghiosoff, Konstantin; Mayr, Herbert(American Chemical Society, ACS, 2016-07-08)
The kinetics and mechanism of the reactions of formyl-stabilized ylide Ph3P═CHCHO (1) and acetyl-stabilized ylide Ph3P═CHCOMe (2) with benzhydrylium ions (Ar2CH+, 3) were investigated by UV–vis and NMR spectroscopy. As ...
Byrne, Peter A.; Gilheany, Declan G.(Wiley, 2016-06-06)
The previous work on the hydrolysis and alcoholysis reactions of phosphonium ylides is summarized and reviewed in the context of their currently accepted mechanisms. Several experimental facts relating to ylide hydrolysis ...
Rate and equilibrium constants of the reactions of nicotine and structurally related compounds with benzhydrylium ions have been determined UV-Vis spectroscopically using stopped-flow and laser-flash techniques. The pyridine ...
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