Halogenations of Anthracenes and Dibenz [a, c] anthracene with N-Bromosuccinimide and N-Chlorosuccinimide1

…, J Turk, J Speigle, J Corbin, J Masnovi…

文献索引：Duan, Shaoming; Turk, Jeff; Speigle, Joseph; Corbin, Jean; Masnovi, John; Baker, Ronald J. Journal of Organic Chemistry, 2000 , vol. 65, # 10 p. 3005 - 3009

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被引用次数: 32

摘要

Halogenation of dibenz [a, c] anthracene (1) by NBS in CCl4 affords the products of 9-and 10-monobromination in the ratio of 9: 1. The reaction is accelerated by iodine, and HBr effects rearrangement of 9-bromo product to the sterically less crowded 10-bromo isomer. The mechanism is proposed to involve reversible addition of Br2, followed by elimination of HBr. Reaction of NCS with 1 in CCl4 requires addition of HCl and affords exclusively 9- ...