PART I. SYNTHESIS OF 2,12-DIBROMOCYCLODODECANOLS AND 3-BROMOCYCLODODECENE OXIDES. PART II. REACTIONS OF ALLYLZINC BROMIDES. PART III. SYNTHESIS OF CYCLOPROPANOL DERIVATIVES

THOMAS ANDREW KILLINGER, Purdue University

Abstract

Part I. Stereoselective syntheses of the isomeric 2,12-dibromocyclododecanols, corresponding acetates, and 3-bromocyclododecene oxides are described. Part II. (A) The use of alcohol as a solvent for the generation and addition of allyliczinc halides to aldehydes and ketones if reported. (B) Attempts to alkylate 1-methylcyclohexene oxide at the tertiary carbon atom using allylzinc, magnesium, and aluminum reagents are described. Part III. The syntheses of exo and endo-6-bicyclo{3.1.0}hexanols, the corresponding acetates, and the isomeric 2,3-dimethylcyclopropanols by the reaction of (alpha),(alpha)' dibromoalcohols with zinc in ethanol are reported.

Degree

Ph.D.

Subject Area

Organic chemistry

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