Trans-β,γ-Hexenolの合成

概要

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Ruzicka's Δ2, 6 ronan.dienal (2-trans-6-?), which was obtained by him from β, γ-hexenol prepared by means of subjecting ethyl ester of sorbic acid to the Bouveault's reduction, is identical with the natural substance, while Hunsdiecker's Δ2, 6 nonandienaI which was derived from 2-penten-Iol and Takei's Δ2'6-nonandienal (2-traps-6-?) from leaf alcohol are different from the natural. type. From the above, fact the latter two are considered to be 2-traps-6-trans, and Ruzicka's to be 2-trans-6-cis. We prepared ethyl-vinylcarbinol (I) from ethyl magnesium bromide, and by subjecting it to allyl-transportation and the Grignard's reaction we could synthesize traps-β, γ-hexenol. 3, 5-Dinitrobenzoate of the last mentioned substance is identical with that of natural leaf-alcohol in having mp. of 495_??_50°C) Hence the stereo form of natural leaf-alcohol is traps-form.
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