7786-21-2Relevant articles and documents
Synthesis of Highly Substituted Phenols and Benzenes with Complete Regiochemical Control
Zhang, Xiaojie,Beaudry, Christopher M.
supporting information, p. 6086 - 6090 (2020/08/12)
Substituted phenols are requisite molecules for human health, agriculture, and diverse synthetic materials. We report a chemical synthesis of phenols, including penta-substituted phenols, that accommodates programmable substitution at any position. This method uses a one-step conversion of readily available hydroxypyrone and nitroalkene starting materials to give phenols with complete regiochemical control and in high chemical yield. Additionally, the phenols can be converted into highly and even fully substituted benzenes.
A New Rearrangement of Alkoxybenzyl Anions
Bates, Robert B.,Siahaan, Teruna J.,Suvannachut, Kessara
, p. 1328 - 1334 (2007/10/02)
Alkyl groups migrate from oxygen to carbon in alkyl aryl ethers which have been metalated in benzylic positions. 2,6-Dimethylanisole provides a variety of 2,6-dialkylphenols and their ethers in 45-80percent yields.Rearrangement products are obtained in 10-30percent yields from other dimethylanisoles and from methylanisoles.The reactions appear to proceed, like Wittig rearrangements, by homolytic cleavage of the alkyl-oxygen bond followed by recombination of the resulting radical pair in a different way.The rearrangements can be avoided by using methyl ethers and working at or below room temperature.
