Aromatic substitutions with rearrangements. Part I. Products of the chlorination of 1-naphthol and some related compounds

Abstract

Structures for the chlorination products of 1-naphthol and some of its derivatives have been clarified by the use of ultraviolet spectroscopy, by which 1-oxo-1,4-dihydronaphthalenes can be distinguished from 1-oxo-1,2-dihydronaphthalenes. The following compounds have been characterised: 2,4,4-trichloro-1-oxo-1,4-dihydro-, 2,2,4-trichloro-1-oxo-1,2-dihydro-, 2,2,3,4-tetrachloro-1-oxo-1,2-dihydro-, 2,3,4,4-tetrachloro-1-oxo-1,4-dihydro-, 2,3,4-trichloro-2-methyl-1-oxo-1,2-dihydro-, and 2,3,4-trichloro-4-methyl-1-oxo-1,4-dihydro-naphthalene. Many of the reactions described can formally be regarded as involving electrophilic substitution with rearrangement (the S_E2′ reaction).