S,S-Dimethyl Dithiocarbonate: A Useful Reagent for Efficient Conversion of Aldoximes to Nitriles

Abstract

Dimethyl dithiocarbonate (DMDTC) has been shown to be an efficient dehydrating agent for a range of oximes derived from aliphatic, aromatic and heteroaromatic aldehydes yielding the corresponding nitriles in high yields.

Key words

DMDTC - nitriles - oximes - dehydration

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10

All nitriles were characterized by comparison of their physical and spectroscopic data with reported data.

11

General Procedure for Preparation of Nitriles: To a solution of the appropriate oxime 2 (1 mmol), DMDTC (0.14 g, 1.1 mmol) and Et₃N (0.70 mL, 5.0 mmol) in dioxane (15 mL) were heated with stirring at 90 °C for 8-11 h (monitored by TLC). Concentration under reduced pressure gave crude product, which was filtered through a short silica gel column using hexane-EtOAc as eluent to give the corresponding nitrile 4.