H. V. D. Haak, H. Plas
Sep 2, 2010
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
The conversion of 1-halogeno-2,7-naphthyridines into the corresponding 1-amino compounds with KNH2/NH3, is shown, by the use of deuterated starting compounds, to proceed via an SN(AE)ipso substitution and not via an SN(AE)tele mechanism, even though convincing evidence for the formation of tele σ-adduct, 8-amino-1-halogeno-dihydro-2,7-naphthyridinide, was obtained. Using the same methods, it is shown that the conversion of 2-bromo-1,8-naphthyridine into 2-amino-1,8-naphthyridine proceeds, to the extent of 40%, via an odd SN(AE)tele pathway.