Some Displacement Reactions of Neopentyl Type Bromide Derived from Thujopsene

概要

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The reaction of thujopsene with gaseous hydrogen bromide at low temperature affords a 48% yield of neopentyl type bromide. The reactivity of the homoallyl bromide was inspected. First, the neopentyl type bromide was derived to a diethyl widdryl malonate in order to demonstrate the reaction which indicates the involvement of homoallylcyclopropylcarbinyl ion system. The malonate was converted to a carboxylic acid and then to isomeric lactone. To demonstrate the reaction which suggests the retention of carbon frame work in the reaction, the reaction of the neopentyl bromide was extended to Grignard reaction. The Grignard reagent reacted with cyclohexanone gave a tertiary alcohol, whereas a dimeric hydrocarbon was also obtained through the Wurtz type condensation. The tertiary alcohol was converted to a dehydrated hydrocarbon and then a glycol.
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