Published Research - Department of Chemistry

 

Date of this Version

1993

Citation

Patent Number: 5,231,205

Comments

Appl. No.: 763,629

Abstract

The magnesium complexes of cyclic hydrocarbons, such as 1,2-dimethylenecycloalkanes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4-diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkyl ditosylates, or bromoalkylnitriles serve as a convenient method for synthesizing spirocyclic systems. Significantly, spirocarbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4- diyl)magnesium complexes with carboxylic esters and acids whereas low temperatures lead to regioselective synthesis of £8,y-unsaturated ketones.

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