The Journal of Organic Chemistry

Mechanism of thietane formation from the reaction of 1, 3-dioxan-2-ones with thiocyanate ion. Stereochemical investigation

LA Paquette, JP Freeman

Index: Paquette,L.A.; Freeman,J.P. Journal of Organic Chemistry, 1970 , vol. 35, p. 2249 - 2253

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Citation Number: 21

Abstract

The stereochemical fate of C-4 in a l13-dioxan-2-one in its decomposition to a 2-substituted thietane has been examined. Lithium aluminum hydride reduction of (R)-(-)-3-acetoxybutyric acid, obtained from quinine resolution of@-hydroxybutyric acid, afforded (R)-(-)-l13- butanediol. This diol was then converted to (E)-(-)-4-methyl-1, 3-dioxan-2-one, which was in turn heated with potassium thiocyanate at 170-180". The resulting thietane was oxidized ...