Ruthenium Tetroxide Oxidation of Simple Ethers: A Systematic Study

Abstract

Since first introduced into organic chemistry by Djerassi¹ in 1953, ruthenium tetroxide has been exploited widely as an effective multipurpose oxidant.³ Unusual in this regard is its apparent ability to oxidize ethers. For example, in their pioneering study of RuO₄ as a multipurpose oxidant, Berkowitz and Rylander⁴ reported the conversion of tetrahydrofuran to γ-butyrolactone. However, to date no systematic study of this application has appeared, although a number of additional examples⁵ in complex systems, notably steroids,⁶ are on record. In connection with our studies which recently culmina-