Aromatic sulfonation. 97. Isomerization and sulfodeprotonation in the reaction of 1, 6-oxido [10] annulene, 1, 6-imino [10] annulene, their isomers 1-naphthol and 1- …

A Koeberg-Telder, H Cerfontain

Index: Koeberg-Telder, Ankie; Cerfontain, Hans Journal of Organic Chemistry, 1986 , vol. 51, # 13 p. 2563 - 2567

Full Text: HTML

Citation Number: 5

Abstract

The reactions of 1-naphthol (3), 1-aminonaphthalene (lo), and 1,6-oxido- (l), 1,6-imino- (2), and ll-oxo- 1,6-methano[lO]annulene (15) with SO3 in aprotic solvents have been studied. With 3 the initial product is 1-naphthyl hydrogen sulfate (4), which is slowly converted into the 1-naphthol-2- (5) and -4-sulfonic acid (6) via 0-desulfonation and C-sulfonation on using <1 equiv of SO3, but via C-sulfonation and 0-desulfonation if the SO3 is in a large excess. It is ...