1-Alkyl-1,2-dihydropyridines thermolyse to complex mixtures, but 1-alkyl-2,3,5,6-tetraphenyl-1,4-dihydropyridines (prepared from the amine and 2,3,5,6-tetraphenylpyrylium salts followed by NaBH4) give alkanes smoothly at ca. 200 °C.
Thermolysis of 1-benzyl-2-deuterio-2,4,6-triphenyl-1,2-dihydropyridine gives ω-monodeuteriotoluene (as shown by 2H n.m.r. spectroscopy) indicating a radical mechanism.
A. R. Katritzky, K. Horvath and B. Plau, J. Chem. Soc., Perkin Trans. 1, 1980, 2554 DOI: 10.1039/P19800002554
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