Selectivity Adjustment in the Cleavage of Allyl Phenyl and Methyl Phenyl Ethers with Boron Trifluoride-Methyl Sulfide Complex

Marek T. Konieczny; Grzegorz Maciejewski; Wojciech Konieczny

doi:10.1055/s-2005-865304

SHORTPAPER

Selectivity Adjustment in the Cleavage of Allyl Phenyl and Methyl Phenyl Ethers with Boron Trifluoride-Methyl Sulfide Complex

Marek T. Konieczny*, Grzegorz Maciejewski, Wojciech Konieczny
Department of Organic Chemistry, Medical University of Gdańsk, Gen. J. Hallera Str. 107, 80-416 Gdańsk, Poland
Fax: +48(58)3493206; e-Mail: markon@amg.gda.pl;

Abstract

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Abstract

Cleavage of model allyl phenyl and methyl phenyl ethers with boron trifluoride-methyl sulfide complex is described. The demonstrated strong dependence of the reaction rate on the substitution pattern of the phenyl ring and the reaction conditions make it potentially possible to selectively cleave a single methoxy (or allyloxy) group in polymethoxy (or allyloxy) compounds.

Key words

ethers - cleavage - regioselectivity - substituent effects - boron trifluoride - methyl sulfide

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References

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