Chinese Journal of Chemistry
Copyright © 2014 SIOC, CAS, Shanghai & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Cover Picture: A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via the o-Quinone Methides Generated from 2-(1-Tosylalkyl)phenols (Chin. J. Chem. 10/2014)
The cover picture shows a concise synthesis of 2-(2-hydroxyphenyl)acetonitriles through reaction of 2-(1-tosylalkyl)phenols and trimethylsilyl cyanide in the presence of base potassium carbonate and tetra-n-butylammonium fluoride (TBAF). 2-(1-Tosylalkyl)phenols generate ortho-quinone methides (o-QM) intermediates under the basic conditions and TBAF serves as an initiator to deliver cyanide anion. Subsequently, o-QM intermediates undergo Michael addition with the cyanide anion to furnish 2-(2-hydroxyphenyl)acetonitriles. Additionally, the adduct 2-(2-hydroxyphenyl)acetonitriles can be conveniently transformed to benzofuranones. This methodology features good yields and the products can be further functionalized. More details are discussed in the article by Zhou et al. on page 981–984.