ChemInform Abstract: Reversible Aromatic Bromination Induced by Buttressing; 1-Bromo- and 8- Bromo-3,6-di-tert-butyl-2-methoxynaphthalene.
✍ Scribed by C. D. BRADDOCK; S. C. TUCKER; J. M. BROWN
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 30 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Reversible Aromatic Bromination Induced by Buttressing; 1-Bromoand 8-Bromo-3,6-di-tert-butyl-2-methoxynaphthalene.
-Bromination of the methyl ether (V), which is prepared via a conveniet synthesis of the alcohol (III), gives a mixture of the 1-brom-and 8-bromo derivatives. The 1-bromo derivative (VI) is formed initially and undergoes proton-catalyzed reversible reaction leading ultimatively to the 8-bromo ether. Steric buttressing by the 3-tert-butyl group is responsible for this fact. Additionally, it is shown that the reactivity of the 1-bromo ether (VI) or its derivatives is different from that of its unsubstituted precursor. -(BRADDOCK, C. D.; TUCKER, S.