The formal oxidative addition of electron-rich transoid dienes to bromonaphthoquinones

…, A Karipides, CT Wigal, SW Heinzman…

Index: Grunwell, John R.; Karipides, Anastas; Wigal, Carl T.; Heinzman, Stephen W.; Parlow, John; et al. Journal of Organic Chemistry, 1991 , vol. 56, # 1 p. 91 - 95

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Citation Number: 81

Abstract

Results We and others2t3 have reported the highly regiospecific conversion of 1, 5-and 1, 8- diacetoxynaphthalene, 5 and 6, to 2-bromo-and 3-bromo-5-acetoxy-l, 4-naphthoquinone, 7 and 8. When 5 or 6 was allowed to stir at 65" C for 1 h in the presence of 4 equiv of N- bromosuccinimide dissolved in aqueous acetic acid, 7 or 8 was afforded in greater than 90% yield. In each case, one regioisomer was produced without any of the other isomer as ...