Unprotected N-H aziridine aldehydes are surprisingly stable compounds which can undergo reactions in the absence of protecting groups. In total, three different transformations were explored during my Master’s thesis. The conversions include the dissociation of the aziridine aldehydes, which exist as dimers, and their subsequent re-dimerization in various solvents. The development of mixed aziridine aldehyde adducts and their attempted modifications will also be discussed. Finally, the discovery of N-H aziridine compounds containing a 1,3-dicarbonyl functionality will be discussed, as will their attempted transformations.

Unprotected N-H aziridine aldehydes are surprisingly stable compounds which can undergo reactions in the absence of protecting groups. In total, three different transformations were explored during my Master’s thesis. The conversions include the dissociation of the aziridine aldehydes, which exist as dimers, and their subsequent re-dimerization in various solvents. The development of mixed aziridine aldehyde adducts and their attempted modifications will also be discussed. Finally, the discovery of N-H aziridine compounds containing a 1,3-dicarbonyl functionality will be discussed, as will their attempted transformations.

No description available.

Thesis (Ph. D.)--University of Chicago, Dept. of Chemistry, August 2000. / Includes bibliographical references. Also available on the Internet.

Thesis--University of Florida. / Description based on print version record. Typescript. Vita. Bibliography: leaves 126-130.

N-alkenyl aziridines are a unique class of molecules that do not behave as typical enamines as a result of the inability of the nitrogen atom lone-pair of electrons to delocalize. The attenuated nucleophilicity of these enamines presents opportunities for selective functionalization and reactivity not available to classical enamines. An operationally simple and mild copper-mediated coupling has been developed that facilitates the preparation of a broad range of N-alkenyl aziridines not available through existing methods. The preparation and reactivity of highly functionalized N-alkenyl aziridines are reported. Also reported is the application of the chemoselective amine/aldehyde/alkyne (A3) multicomponent coupling involving amphoteric aziridine aldehydes as the aldehyde component. This coupling allows access to propargyl amines with pendent aziridine functionality.

N-alkenyl aziridines are a unique class of molecules that do not behave as typical enamines as a result of the inability of the nitrogen atom lone-pair of electrons to delocalize. The attenuated nucleophilicity of these enamines presents opportunities for selective functionalization and reactivity not available to classical enamines. An operationally simple and mild copper-mediated coupling has been developed that facilitates the preparation of a broad range of N-alkenyl aziridines not available through existing methods. The preparation and reactivity of highly functionalized N-alkenyl aziridines are reported. Also reported is the application of the chemoselective amine/aldehyde/alkyne (A3) multicomponent coupling involving amphoteric aziridine aldehydes as the aldehyde component. This coupling allows access to propargyl amines with pendent aziridine functionality.

The enantioselective chlorination of alcohols by the menthyldipheny1-phosphine/carbon tetrachloride reagent previously reported in the literature was investigated and quantified. Further examples were found. A new enantioselective reaction of menthyldipheny1phosphine/carbon tetrachloride was discovered. This was the synthesis of aziridines by ring closure of ? amino alcohols. Other optically active phosphines in conjunction with carbon tetrachloride were found to react in a similar manner to menthy1dipheny1phosphine/carbon tetrachloride with a variety of ? amino alcohols. Menthy1dipheny1phosphine was found to react enantioselectively with a ? amino alcohol in the presence of chlorine.

Thesis (Ph. D.)--Ohio State University, 2003. / Title from first page of PDF file. Document formatted into pages; contains xx, 256 p.: ill. (some col.). Includes abstract and vita. Advisor: Stephen C. Bergmeier, College of Pharmacy. Includes bibliographical references (p. 234-256).

Univ., Diss., 2009--Kassel.