Alkyl nitrite-metal halide deamination reactions. 7. Synthetic coupling of electrophilic bromination with substitutive deamination for selective synthesis of multiply …

…, MA Van Lente, R Mowat, WF Fobare

Index: Doyle, Michael P.; Lente, Michael A. van; Mowat, Rex; Fobare, William F. Journal of Organic Chemistry, 1980 , vol. 45, # 13 p. 2570 - 2575

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Citation Number: 32

Abstract

Aromatic amines undergo oxidative substitution with copper (I1) bromide that is in competition with substitutive deamination when these reactions are performed with tert-butyl nitrite. Except for the exceptionally reactive 4-substituted 1-aminonaphthalenes, which undergo selective bromine substitution at the 1-and 2-positions in relatively high isolated yields, rates for oxidative bromination and substitutive deamination are not sufficiently ...