Direct observation of the reaction of the quinone-methide from 5,6-dihydroxyindole with the nucleophilic azide ion

✍ Scribed by Akeel T. Al-Kazwini; Peter O'Neill; Robert B. Cundall; Gerald E. Adams; Alex Junino; Jean Maignan

• Book ID: 104216076
• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 235 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79596-7

✦ Synopsis

Investigation of the oxidation of mclanagenic intermediates and, in particular, the ultimate oxidative polymerisation of 56-dihydroxyindole

(1) is important for a comprehensive understanding of the biosynthesis of melanin. Oxidation of 1 leads to the formation of its corresponding quinone methide, a reactive intermediate. We report a novel approach using a fast reaction technique to produce the quinone methide of 1 &&J and study its chemistry. In aqueous solution at pH 9, the quinone methide has a lifetime of < 0.