The redn. of 1-methyl-4-cyano-pyridinium iodide at -45 in 0.8N methanolic NaOH yielded 60% trans-cis-trans-7,8-dicyano-4,11-dimethyl-4,11-diazatricyclo-[6.4.0.02.7] dodeca-5,9-diene (I) contg. only traces of II. Redns. performed at temps. increasing from -45 to -20, yielded ppts. contg. progressively more II, until at > -20 only II was present in the ppt. I was very labile and, in the solid state, at 15-20 was quickly converted to II. If I was rapidly poured into 6N HCl at -45, an insol. product which was sufficiently stable for characterization was immediately formed.
Borohydride reduction of pyridinium salts. IV. Simultaneous low-temperature formation of (2+2) and (4+2) cycloadducts in the reduction of 1-methyl-4-cyanopyridinium iodide / Liberatore, Felice; Casini, Antonio; Carelli, Vincenzo; Arnone, A.; Mondelli, R.. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 41:(1971), pp. 3829-3832.
Borohydride reduction of pyridinium salts. IV. Simultaneous low-temperature formation of (2+2) and (4+2) cycloadducts in the reduction of 1-methyl-4-cyanopyridinium iodide.
LIBERATORE, Felice;CASINI, Antonio;CARELLI, Vincenzo;
1971
Abstract
The redn. of 1-methyl-4-cyano-pyridinium iodide at -45 in 0.8N methanolic NaOH yielded 60% trans-cis-trans-7,8-dicyano-4,11-dimethyl-4,11-diazatricyclo-[6.4.0.02.7] dodeca-5,9-diene (I) contg. only traces of II. Redns. performed at temps. increasing from -45 to -20, yielded ppts. contg. progressively more II, until at > -20 only II was present in the ppt. I was very labile and, in the solid state, at 15-20 was quickly converted to II. If I was rapidly poured into 6N HCl at -45, an insol. product which was sufficiently stable for characterization was immediately formed.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
