Issue 5, 1973

The acid-catalysed hydrolysis of tetramethyloxiran: a re-investigation

Abstract

The acid-catalysed hydrolysis of tetramethyloxiran yields 2,3-dimethylbutane-2,3-diol (ca. 98%) and 3,3-dimethylbutan-2-one (<1%). This result differs markedly from that previously reported and widely quoted as evidence for a free carbonium ion. It must now be concluded that reaction involves bimolecular attack by water on the protonated epoxide.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1973, 518-520

The acid-catalysed hydrolysis of tetramethyloxiran: a re-investigation

M. D. Carr and C. D. Stevenson, J. Chem. Soc., Perkin Trans. 2, 1973, 518 DOI: 10.1039/P29730000518

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