ChemInform Abstract: Oxidative Reactions of Azines. Part 3. Synthesis and Oxidation of 1,2,3,6-Tetrahydro-4-([2,2]paracyclophan-4-yl)pyridines.
Abstract
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ChemInform Abstract
The cyclocondensation of the [2.2]paracyclophanylpropene (I) with formaldehyde and amines gives a mixture of piperidinol derivative (IV) and tetrahydropyridyl derivative (V). The piperidinol easily undergoes dehydration in hydrochloric acid to improve the yield of the title tetrahydropyridine (V). While aromatization occurs in the thermal reaction of (V) with sulfur, under oxidative conditions the tetrahydropyridinone (VI) is formed. Thus, the introduction of the bulky paracyclophanyl group prevents the previously observed hydroxylation of the double bond of the tetrahydropyridine (V) under the action of permanganate ions.
