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

R.G.F. Giles; I.R. Green; L.S. Knight; V.R.L. Son; P.R.K. Mitchell; S.C. Yorke

doi:10.1039/P19940000853

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

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

R.G.F. Giles, I.R. Green, L.S. Knight, V.R.L. Son, P.R.K. Mitchell and S.C. Yorke

Journal of the Chemical Society, Perkin Transactions 1, (7), pp.853-857

1994

DOI: https://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.

Details

Title: Regioselective bromination, debromination and bromine migration in a 2-acetoxymethyl-4,5,7-trialkoxynaphthalene
Authors/Creators: R.G.F. Giles (Author/Creator)
I.R. Green (Author/Creator)
L.S. Knight (Author/Creator)
V.R.L. Son (Author/Creator)
P.R.K. Mitchell (Author/Creator)
S.C. Yorke (Author/Creator)
Publication Details: Journal of the Chemical Society, Perkin Transactions 1, (7), pp.853-857
Publisher: Royal Society of Chemistry
Identifiers: 991005540312807891
Murdoch Affiliation: Murdoch University
Language: English
Resource Type: Journal article

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