The kinetics and mechanisms of aromatic halogen substitution. Part XXIV. The stereochemistry of addition of chlorine to naphthalene
- 1 January 1966
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 827-833
- https://doi.org/10.1039/j29660000827
Abstract
The reaction of chlorine with naphthalene in acetic acid gives products of substitution (mainly 1-chloronaphthalene); products of addition of chlorine (mainly naphthalene-α-tetrachloride, m. p. 182°); and other products of addition (mainly an acetoxytrichloride). In the presence of added lithium chloride, the mixture of tetrachlorides contains a major proportion of the stereoisomeric δ-isomer, m. p. 96°. Light-catalysed addition in carbon tetrachloride gives a mixture of isomers, the least soluble being naphthalene-γ-tetrachloride, m. p. 134°, and the major part of the remainder being a new isomer, naphthalene-ε-tetrachloride, m. p. 85–87°. The configurations and conformations of the γ-, δ-, and ε-tetrachlorides and of the acetoxytrichloride have been established by proton magnetic resonance spectroscopy. The results establish that the α-tetrachloride is not formed through capture of a carbonium ionic intermediate by chloride ion from the environment.Keywords
This publication has 0 references indexed in Scilit: