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Hydroxylation and Amination of Azulenes by Vicarious Nucleophilic Substitution of Hydrogen (2000)

Makosza, Mıˇeczysław ; Podraza, Renata

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 193-198

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ISSN: 1434-193X

Keywords: Nucleophilic substitutions ; Azulenes ; Hydroxylation ; Amination ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---Hydroxylation of azulenes with tert-butylhydroperoxide proceeds efficiently at the 6-position when the former contain electron-withdrawing substituents in the five-membered ring. Similarly, VNS amination of azulenes proceeds with 4-amino-1,2,4-triazole; its anion, being an active nucleophile, also reacts with unsubstituted azulene. A variety of transformations of 6-hydroxyazulenes, such as substitution of the corresponding sulfonates with nitrogen, oxygen, sulfur, carbon nucleophiles and halogens, and the Claisen rearrangement of allylic ethers, is reported.

Type of Medium: Electronic Resource

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