113603-13-7Relevant academic research and scientific papers
Investigations about the Reducing Properties of Dimeric Dihydropyridines
Pragst, F.,Santrucek, M.
, p. 67 - 80 (2007/10/02)
The reaction of a series of bis- derivatives P2 with some benzyl halides, trans-1,2-dibromoethane and several heteroaromatic cations Q+ was investigated in acetonitrile/toluene with electrochemical and kinetic methods.For substrates with a reduction potential between -0.9 and -1.5 V the reaction occurs via the ratedetermining dissociation of P2 into free radicals P. as the real reducing agents, which transform the benzyl halides into the corresponding 1,2-diarylethanes and Q+ into the corresponding dimeric product Q2.For thereduction of trans-1,2-dibromocyclohexane to cyclohexene a simultaneous transfer of two electrons to the substrate combined with the dissociation of P2 into two pyridinium ions P+ is proposed.In the case of a reduction potential more positive than -0.9 V (e.g. nitro substituted benzyl halides) P2 itself can act as the reducing agent with an increased reaction rate.With pyrylium ions Q+ a product P-Q was detected by voltammetry and mass spectroscopy.In this case an electrophilic attack onto P2 instead of the electron transfer from P2 to Q+ cannot be excluded.
