Aromatization reaction by nucleophilic attack of cyanide ion upon a sulfonylated myo-inositol

Autor: María E. Gelpi, Raúl A. Cadenas, Jorge Mosettig
Rok vydání: 1981
Předmět:
Zdroj: Carbohydrate Research. 98:51-56
ISSN: 0008-6215
DOI: 10.1016/s0008-6215(00)87140-2
Popis: The reaction of 2,3-di- O -acetyl-1,4,5,6-tetra- O -(methylsulfonyl)- myo -inositol with potassium cyanide in 2-methoxyethanol gave as the final product, through a series of rearrangements and eliminations, 4-cyano-1- O -(methylsulfonyl)-1,2-benzene-diol, whose structure was ascertained by n.m.r. and mass spectrometry. The intermediate displacement of a mesyloxy group through intramolecular attack of an oxide anion, favored by an electrostatic-field effect of the cyano group, is postulated to explain this reaction.
Databáze: OpenAIRE