The Journal of Organic Chemistry

The use of [2, 3] sigmatropic rearrangements for the specific ortho-substitution of polycyclic aromatic amines. The methylation of naphthylamines and the synthesis of …

PG Gassman, WN Schenk

Index: Gassman,P.G.; Schenk,W.N. Journal of Organic Chemistry, 1977 , vol. 42, p. 3240 - 3243

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Citation Number: 18

Abstract

Procedures have been developed for the specific ortho-alkylation of polycyclic aromatic amines. Both a-and 6-naphthylamine have been ortho-methylated by a procedure involving sequential treatment of the amine with (a) tert-butyl hypochlorite,(b) dimethyl sulfide,(c) sodium methoxide, and (d) Raney nickel. This procedure, which uses a [2, 3] sigmatropic rearrangement of an ylide in the key ring functionalization step, gave only ortho- ...