Abstract

Reactions of 1-ethylspiro[2.5]oct-1-ene and triethylaluminum furnish a product that results from addition of triethylaluminum to the double bond with opening of the three-membered ring to form an allylic organoaluminum compound and a second product that results from addition of this allylic organoaluminum compound to the cyclopropene double bond. Reactions of spiro[2.5]oct-1-ene with triethylaluminum furnish two products resulting from addition to the cyclopropene double bond, one of triethylaluminum and the other of an allylic organoaluminum compound formed by addition of triethylaluminum to the cyclopropene double bond with opening of the three-membered ring. Reactions of the spiro compounds with triethylboron, triethylgallium, diethylzinc, or diethylcadmium also furnish rearrangement products, but reactions with diethylmagnesium or ethyllithium furnish only addition products.

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