Interaction of magnesium indolates and allyl oxides in the presence of bis (triphenylphosphine)nickel dichloride results in indole /3-allylation, except in cases involving highly substituted indoles and allyl alcohols. This method permits the /3-prenylation of indole and -prenylation of ketones (by way of their magnesium enaminates). Base-induced interaction of ethynyldimethylcarbinyl chloride and indole under a variety of conditions yields ß-(/3,/3-dimethylvinyl)quinoline as well as variously dehydroprenylated indoles. -Lithiation of iV-(benzenesulfonyl)indole followed by treatment with prenyl bromide or ß,/3-dimethylacrylyl chloride produces a-prenylor a-oxoprenylindole derivatives, the sodium amalgam reduction of the former of which yields a-prenylindole. Interaction of d-cuprated N-(benzenesulfonyl)indole with the same halides followed by reduction affords ßprenylindole and /3-oxoprenylindole, the latter also being the product of the reaction of magnesium indolate and the acid chloride. Lithium aluminum hydride reduction of l-(benzenesulfonyl)-3-oxoprenylindole affords an alcohol, whose base hydrolysis produces /3-dehydroprenylindole, a compound whose dimerization has led previously to naturally occurring yuehchukene.

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