873292-81-0Relevant articles and documents
New reagents for the synthesis of arylmethyl ethers and esters
Albiniak, Philip A.,Dudley, Gregory B.
scheme or table, p. 841 - 851 (2010/07/10)
This Account chronicles efforts leading up to the development of new arylmethyl transfer (benzylation) reagents for protecting oxygen functional groups under relatively mild and neutral conditions. It begins with an investigation of organosiletanes as surrogate hydroxyl groups, which inspired siletane-functionalized benzyl ethers and forced us to confront the difficulties associated with the synthesis of benzyl ethers. The end result is a new series of neutral oxypyridinium salts for the benzylation of various nucleophilic functional groups under mild conditions. 1 Introduction 2 Tamao-type Oxidation of Strained Organosiletanes 3 p-Siletanylbenzyl (PSB) Protecting Groups 4 2-Benzyloxy-1-methylpyridinium Triflate 5 Friedel-Crafts Reactions and Mechanistic Insights 6 Benzyl Ester Formation 7 Substituted Benzyl Transfer Reagents 8 Conclusions and Outlook. Georg Thieme Verlag Stuttgart New York.
p-siletanylbenzylidene acetal: Oxidizable Protecting group for diols
House, Sarah E.,Poon, Kevin W. C.,Lam, Hubert,Dudley, Gregory B.
, p. 420 - 422 (2007/10/03)
Hydrogen peroxide oxidation of benzylidene acetals (and derivative benzyl ethers) that incorporate a siletane ring at the para position creates a deprotection pathway without affecting other important chemical properties of the benzylidene acetal, such as
