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Communication | Special issue | Vol 15, No. 1, 1981, pp.179-182
Published online, 1st January, 1970
DOI: 10.3987/S-1981-01-0179
Modified Crown Ether Catalysts. 4. Cleavage of Macrocyclic Ethers by Eaton’s Reagent (Methanesulfonic Acid / Phosphorous Pentoxide)

Paul E. Stott, Jerald S. Bradshaw,* and W. Wesley Parish

*Department of Chemistry, Brigham Young University, Provo, UT 84602, U.S.A.

Abstract

Eaton’s reagent (methanesulfonic acid/phosphorous pentoxide) is a superior media for the acylation of benzo crown ether compounds. Benzo-15-crown-5 was cleaved in Eaton’s reagent to form methansulfonate esters of the glycol cleavage products. A comparison of the NMR spectrum of the cleavage products with those of some of the possible products showed that the aliphatic glycols formed the major portion of the cleavage products.