Reactivity of new precursors of quinone methides

✍ Scribed by Bernard Loubinoux; Joseph Miazimbakana; Philippe Gerardin

• Book ID: 104229771
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 215 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)99619-9

✦ Synopsis

The azidomethylene protecting group allows the synthesis of unstable phenolic compounds which are used as quinone methide precursors in the alkylations of alcohols, phenols, azide, thiophenol, amines, enols and enolates.

The use of the azidomethylene group to protect the hydroxyl functional group allows the phenol to be retrieved under very mild conditions.1 In this way, certain unstable phenols can be prepared in high yield. This is the case of phenols I and JJ, in particular, and of compounds of analogous structure. A few molecules of this type have been isolated and described in the literature.2.3S4 We have noticed that many others were isolable only with great difficulty.