ELECTROPHILIC SUBSTITUTION IN ACENAPHTHENE AND RELATED COMPOUNDS .2. BROMINATION AND CHLORINATION OF BROMO- AND CHLOROACENAPHTHENES

3-Bromo, 3-chloro-, 5-bromo-, and 5-chloroacenaphthene have been brominated and chlorinated and the products identified. The 3-halo compounds undergo further substitution almost completely in the 6 position. 5-Bromo- and 5-chloroacenaphthenes react with sulfuryl chloride to give, mainly, 5,6-dihalo compounds. Sidechain bromination of 5-bromoacenaphthene is found under a variety of conditions. However, reaction with bromine vapor gives small amounts of 3,5- and 3,6-dibromoacenaphthenes while bromination with hypobromous acid gives 5,6-dibromoacenaphthene as the major product. © 1969, American Chemical Society. All rights reserved.