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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 7
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Original Articles

Bismuth trichloride–mediated cleavage of phenolic methoxymethyl ethers

Oghale Obaro-BestDepartment of Chemistry, State University of New York at Plattsburgh, Plattsburgh, New York, USA
,
Jack ReedDepartment of Chemistry, State University of New York at Plattsburgh, Plattsburgh, New York, USA
,
Alya A. F. B. NorfadilahDepartment of Chemistry, State University of New York at Plattsburgh, Plattsburgh, New York, USA
,
Ryan MonahanDepartment of Chemistry, State University of New York at Plattsburgh, Plattsburgh, New York, USA
&
Rajesh SunaseeDepartment of Chemistry, State University of New York at Plattsburgh, Plattsburgh, New York, USACorrespondence[email protected]
Pages 586-593 | Received 16 Feb 2016, Published online: 08 Apr 2016
 
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ABSTRACT

A simple and efficient method for removal of phenolic methoxymethyl ethers in the presence of 30 mol% of bismuth trichloride in acetonitrile/water is described. Notable features of the cleavage protocol entail use of an ecofriendly bismuth reagent, ease of handling, low cost, operational simplicity, and good functional group compatibility. A number of structurally varied phenolic methoxymethyl ethers were cleaved in good to excellent yields.

GRAPHICAL ABSTRACT

Acknowledgments

We thank J. Jones for NMR measurements and S. Blair, B. Rosenthals, M. McNaught, and N. Danyashah for assistance for preparing phenolic MOM ethers 2a, 4a, 8a, and 16a respectively.

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