A Dehydrohalogenation Methodology for Synthesizing Terminal Olefins under Mild Conditions

Abstract

A new methodology for preparing terminal olefins in good yield by dehydrohalogenation of primary alkyl iodide with tetrabutylammonium fluoride in dimethyl sulfoxide at room temperature is presented. Optimization of the mild reaction conditions and assays on various alkyl iodides are described.

Key words

alkenes - alkyl halides - elimination - dehydrohalogenation - tetrabutylammonium fluoride

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7

No alkene was observed when a primary alkyl iodide (1-iodododecane) was treated with DBU in benzene or DMSO at r.t. or at 90 °C.