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Electrophilic acetylation and bromination reactions of benzo[ b ]naphtho[2,3‐ e ][1,4]dioxin
Author(s) -
Piórko Adam,
Crook Michelle,
Sampson Peter
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290640
Subject(s) - chemistry , halogenation , bromine , electrophile , reactivity (psychology) , acetylation , electrophilic substitution , medicinal chemistry , derivative (finance) , electrophilic aromatic substitution , selectivity , organic chemistry , catalysis , medicine , biochemistry , alternative medicine , pathology , financial economics , economics , gene
The reactivity of benzo[ b ]naphtho[2,3‐ e ][1,4]dioxin in the electrophilic aromatic substitution reactions has been studied. Friedel‐Crafts acetylation resulted in the formation of three out of the possible five monoacetylated products, with the acetyl group located in positions 8 (major), 7 and 6 (minor) of the heterocycle. In the bromination reaction a higher selectivity was observed with the 6‐bromo derivative found as the only monobrominated product and the 6,11‐dibromo derivative found as the only polybrominated product. A ratio of unreacted heterocycle:6‐bromo:6,11‐dibromo derivatives in the bromination reaction has been found to depend strongly on the reaction conditions and on the heterocycle:bromine ratio.