Tetrahedron

The acid-catalyzed hydrolysis of 3-oxetanols: An hydroxymethyl group migration in the conversion of 2, 2, 3-trimethyl-3-oxetanol into 3-methyl-3-hydroxymethyl-2- …

J Kagan, JT Przybytek

Index: Kagan,J.; Przybytek,J.T. Tetrahedron, 1973 , vol. 29, p. 1163 - 1167

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Citation Number: 7

Abstract

The acetone photodimer 2, 2, 3-trimethyl-3-oxetanol was synthesized by photocyclization of isopropyloxyacetone and of 3-methyl-3-methoxy-2-butanone. The oxetanol was very sensitive to acids, and it rearranged to 3-hydroxymethyl-3-methyl-2-butanone by ring opening and migration of the hydroxymethyl group.