Regioselectivity in the alkaline thiolate deprotection of aryl methyl ethers

JA Dodge, MG Stocksdale, KJ Fahey…

Index: Dodge, Jeffrey A.; Stocksdale, Mark G.; Fahey, Kennan J.; Jones, C. David Journal of Organic Chemistry, 1995 , vol. 60, # 3 p. 739 - 741

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Citation Number: 43

Abstract

The masking of the phenol moiety as its methyl ether is a ubiquitous protective group tactic'in organic synthesis. While such functionality provides excellent protection against a variety of reagents and experimental conditions, harsh reaction protocols (eg, refluxing HBr2) have been historically required to liberate the parent phenol. This is due, in large part, to the inherent chemical stability of this particular ether linkage." his caveat has contributed to ...