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Brignell, Peter John (1964) Reactions and rearrangements of heterocyclic nitrogen compounds. Doctoral thesis, Sir John Cass College.
A reaction of a 4-chloromethyl-l,4-dihydropyridine with potassium cyanide has been investigated. The product is proved not to be the corresponding 4-cyanomethyl-l,4-dihydropyridine as reported in the literature but has been assigned a. 4-cyano-4,5- dihydroazepine structure. Some other reactions of the 4-chloromethyl -1,4-dihydropyridine have been briefly examined.
The mechanism of the reaction has been investigated. It is postulated that the dihydropyridine is converted to the anion in a reversible, second order, base catalysed reaction to form an intermediate, a 4-H-azepine derivative. It has been demonstrated that the intermediate then reacts rapidly with cyanide ion to yield the dihydroazepine.
Some 1,4-dihydropyridines have been prepared and their ultraviolet spectra examined. The spectral shifts of the n→π. band are discussed and the spectra of some 1,4-dihydropyridine anions and cations are also described.
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