Tetrahedron letters

Sequential and tandem oxidation/acetalization procedures for the direct generation of acetals from alcohols

BM Smith, AE Graham

Index: Smith, Brendan M.; Graham, Andrew E. Tetrahedron Letters, 2007 , vol. 48, # 28 p. 4891 - 4894

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Citation Number: 17

Abstract

Our initial studies considered the one-pot tandem oxidation/acetalization reaction of benzyl alcohol with manganese dioxide in the presence of an excess of trimethyl orthoformate and catalytic quantities of indium triflate. Disappointingly, while these reactions produced benzaldehyde, only small quantities of the desired acetal (∼10%) were observed. We assumed that this may be due to hydrolysis of the orthoformate or of the acetal product under the reaction conditions ...