Selwyn Yorke - Regioselective bromination, debromination and bromine migration in a 2-acetoxymethyl-4,5,7-trialkoxynaphthalene

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  Publication Details (including relevant citation   information):

  Journal of the Chemical Society, Perkin Transactions 1:    Organic and Bio-Organic Chemistry (1972-1999) (1994), (7), 853-7


  Dibromination of   2-acetoxymethyl-4-isopropoxy-5,7-dimethoxynaphthalene (10) in   buffered soln. afforded the 3,8-dibromo deriv. (13) (shown as   structure I).  Similar monobromination of 10 yielded the   8-bromo compd. (15), whereas monobromination in the absence of   the buffer yielded the isomeric 1-bromo compd. (16).    Conversion of 15 into 16 was effected with HO2CCF3.    Selective monodebromination of the dibromo compd. 13 gave rise to   a 3rd isomer, the 3-bromo compd. (18).

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