The 1,6-dihydropyridine I, obtained by NaBH4 redn. of 2-cyano-1-methylpyridinium iodide, undergoes a thermal dimerization to give the cyclobutane deriv. II. II rearranges, by heating, to the isomeric ethenonaphthyridine III (R = H). Label scrambling observed at 110 in III (R = H) reveals a degenerate thermal [3.3] sigmatropic shift.
Borohydride reduction of pyridinium salts. V. Thermal dimerization of 1,6-dihydro-1-methylpyridine-2-carbonitrile / Liberatore, Felice; Casini, Antonio; Carelli, Vincenzo; Arnone, A; Mondelli, R.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 40:(1975), pp. 559-563.
Borohydride reduction of pyridinium salts. V. Thermal dimerization of 1,6-dihydro-1-methylpyridine-2-carbonitrile.
LIBERATORE, Felice;CASINI, Antonio;CARELLI, Vincenzo;
1975
Abstract
The 1,6-dihydropyridine I, obtained by NaBH4 redn. of 2-cyano-1-methylpyridinium iodide, undergoes a thermal dimerization to give the cyclobutane deriv. II. II rearranges, by heating, to the isomeric ethenonaphthyridine III (R = H). Label scrambling observed at 110 in III (R = H) reveals a degenerate thermal [3.3] sigmatropic shift.File allegati a questo prodotto
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