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Date of Award


Document Type


Degree Name

Doctor of Philosophy (Ph.D.)



First Advisor

Emerson G. Cobb

First Committee Member

John R. Tundall

Second Committee Member

Richard P. Dodge

Third Committee Member

David S. Yoder

Fourth Committee Member

Charles A. Matuszak

Fifth Committee Member

Donald K. Wedegaertner


Much information has been obtained on the orientation of unsymmetrical reagents about substituted allenes. Although hydrogen halide addition to 1,2-propadiene yields 2-halopropenes,20,31 it has been ample demonstrated, at least in the case of halogenation and oxymercuration of the 1,2-alkyl substituted allenes, that the attacking electrophile ends up in the product attached to the central carbon of the original allenic system. 20,22,31,34,38,39,40 Using optically active 1,3-dimethylallene(15) it has been shown that the bromination and oxymercuration of 15 is stereospecific. 22,39Knowledge of the absolute configurations of the optically active addition products have made it possible to propose a plausible mechanism for the reactions (eq 1).

1,2-cyclononadiene(1) was brominated in methanol and a 40:60 mixture of two products corresponding to isomeric bromomrthoxycyclonenes was obtained. Preliminary, chemical, and spectral evidence indicated that the isomeric mixture definitely did not consist of cis-trans geometric isomers. The primary objective of the research then became the identification of the isomeric bromination products of 1,2-cyclononadiene(1) in various reactive solvents. The results are discussed with reference to the intermediates that may be involved in these reactions.



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