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Stereochemical Studies of Nitrosamines: The Induced Circular Dichroism of Achiral Nitrosasmines

Description: The induced circular dichroism (ICD) of several chiral nitrosamines and various chiral reagents has been investigated. The interaction is attributed to a 1:1 hydrogen bonded complex between the NO group of the nitrosamine and the hydroxyl groups of alcohols and polyols, or the amino group of amines. Only those chiral reagents possessing large differences in size of the groups about the hydrogen bonding site contributed to CD anomalies. The acyclic 2-octanols did not give observable Cotton effects, presumably due to the similarity in size of the methyl and methylene groups and rotational freedom of the acyclic system. The signs of the Cotton effects could be correlated with the absolute configuration of the sterically hindered alcohols and amines. Only the alpha, axial hydrogens of conformationally biased, heterocyclic nitrosamines were found to undergo selective hydrogen-deuterium exchange, suggesting that this feature is critical for nitrosamine carcinogenicity.
Date: August 1980
Creator: Fribush, Howard M.
Partner: UNT Libraries

Reactions of Anions of Cyclic Oximes, Oxime Ethers, and Chiral Imines

Description: The purpose of this investigation is to examine reactions of anions of oximes, oxime ethers and imines with acylating agents and other electrophiles. It is also an attempt to utilize the phenomenon of geometrical enantiomeric isomerism, in which absolute configuration is determined by double bond geometry, and the concept of regiospecific anion formation, also determined by double bond geometry, for stereospecific synthesis of tropinone derivatives.
Date: August 1980
Creator: Maloney, John R.
Partner: UNT Libraries

Synthesis and Reactions of Some N-Nitrosamines

Description: Nucleophiles react with the α-acetoxy derivative of α-hydroxybenzylbenzylnitrosamine at the carbonyl carbon of the acetoxy moiety followed by fragmentation to the very same intermediates formed by oxidative metabolism. Since α-acetoxybenzylbenzylnitrosamine has been shown to be able to acylate nucleophiles and since the nucleic acids are nucleophiles, then it is possible that this compound may cause mutations by an acylation pathway instead of or in addition to the more common alkylation pathway. The data in Part I of this dissertation should be considered in any further biological investigations of N,N-dialkylnitrosamine induced mutagenesis or carcinogenesis. The study of the synthesis, reactions, mutagenicity, and the possible correlation to compound liposolubility of cyclic N-nitrosamines was also investigated.
Date: December 1982
Creator: Gunn, Valerie E. (Valerie Elizabeth)
Partner: UNT Libraries