Tetrahedron

A unique and highly remarkable boron Trifluoride catalyzed rearrangement Of 2, 2-di-t-butyloxirane into 2, 2, 3, 3, 4, 4-hexamethyltetrahydrofuran

N De Kimpe, L De Buyck, R Verhé, N Schamp

Index: Kimpe, Norbert De; Buyck, Laurent De; Verhe, Roland; Schamp, Niceas Tetrahedron, 1984 , vol. 40, # 17 p. 3291 - 3294

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Citation Number: 4

Abstract

-The boron trifluoride catalyzed rearrangement of 2, 2-di-t-butyloxirane, involving competitive reactions of transient carbenium ions, could be selectively directed towards either 2, 2, 3, 3, 4, 4-hexamethyltetrahydrofuran or 2-t-butyl-2, 3-dimethyl-3-buten-1-ol. Hydride shift to afford 2, 2-di-t-butylacetaldehyde was only observed to a minor extent.