Use of Dimethyldioxirane for the Oxidation of 1,2-Dithiolan-3-ones to 1-Oxides or 1,1-Dioxides. Preparation of 3H-1,2-Benzodithiol-3-one 1,1-Dioxide (Beaucage Sulfurizing Reagent)

Vicente Marchán; Mariona Gibert; Angel Messeguer; Enrique Pedroso; Anna Grandas

doi:10.1055/s-1999-3692

Synthesis 1999; 1999(1): 43-45
DOI: 10.1055/s-1999-3692

short paper

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Use of Dimethyldioxirane for the Oxidation of 1,2-Dithiolan-3-ones to 1-Oxides or 1,1-Dioxides. Preparation of 3H-1,2-Benzodithiol-3-one 1,1-Dioxide (Beaucage Sulfurizing Reagent)

Vicente Marchán^* , Mariona Gibert, Angel Messeguer, Enrique Pedroso, Anna Grandas

^*Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, E-08028 Barcelona, Spain; E-mail: grandas@admin.qo.ub.es

Abstract

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Quantitative oxidation of 3H-1,2-benzodithiol-3-one to 3H-1,2-benzodithiol-3-one 1,1-dioxide (Beaucage sulfurizing reagent) is achieved by reaction of the dithiolanone with a fourfold molar excess of dimethyldioxirane for 2-4 hours at room temperature. A one- or twofold molar excess of reagent affords the 1-oxide as the main product.

oligonucleotides - phosphorothioates - sulfurization - dimethyldioxirane - Beaucage reagent

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