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

Giles, R.G.F., Green, I.R., Knight, L.S., Son, V.R.L., Mitchell, P.R.K. and Yorke, S.C. (1994) Regioselective bromination, debromination and bromine migration in a 2-acetoxymethyl-4,5,7-trialkoxynaphthalene. Journal of the Chemical Society, Perkin Transactions 1 (7). pp. 853-857.

Link to Published Version: http://dx.doi.org/10.1039/P19940000853
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Abstract

Dibromination of 2-acetoxymethyl-4-isopropoxy-5,7-dimethoxynaphthalene 10 in buffered solution afforded the 3,8-dibromo derivative 13. Similar monobromination of compound 10 yielded the 8-bromo compound 15, whereas monobromination in the absence of the buffer yielded the isomeric 1-bromonaphthalene 16. Conversion of 15 into 16 was effected with trifluoroacetic acid. Selective monodebromination of the dibromo compound 13 gave rise to a third isomer, the 3-bromo compound 18.

Publication Type: Journal Article
Publisher: Royal Society of Chemistry
Copyright: © 1994 Royal Society of Chemistry
URI: http://researchrepository.murdoch.edu.au/id/eprint/35911
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