Date of Award

1988

Degree Type

Dissertation

Degree Name

Ph.D.

Department

Chemistry and Biochemistry

Keywords

Chemistry, Organic.

Rights

CC BY-NC-ND 4.0

Abstract

Part I. The synthesis of homochiral 2-methyl-1-azoniatricyclo (4.4.3.0$\sp{1,6}$) tridecane and 2-methyl-1-azonia-tricyclo (4.4.4.0$\sp{1,6}$) tetradecane salts 6 and 7 starting from L-glutamic acid and L-alanine respectively and their applications in phase-transfer catalysis are described. The application of these salts in the enantioselective phase-transfer catalyzed cyclopropanation reaction between diethyl bromomalonate and methyl vinyl ketone, 2-chloroacrylonitrile or acrolein gave products in good chemical yields, but the enantiomeric excess of the products was very low. Alkylation reactions with ethyl 2-oxocyclopentanecarboxylate or ethyl 2-oxocyclohexanecarboxylate and allyl bromide proceed to give products in good yields but with very low enantiomeric excess. Possible reasons for these results are discussed. Part II. The synthesis of some N-($\omega$-carboxyalkyl)lactams and N-($\omega$-carbethoxyalkyl)lactams and their pyrolysis over soda lime to give enamines are described. This investigation took place as part of a general investigation of the effectiveness of this carbon-carbon bond forming reaction in the synthesis of enamines and iminium salts and the ability to utilize this method in the synthesis of 1-azapropellanes with different ring sizes.Dept. of Chemistry and Biochemistry. Paper copy at Leddy Library: Theses & Major Papers - Basement, West Bldg. / Call Number: Thesis1988 .A363. Source: Dissertation Abstracts International, Volume: 49-04, Section: B, page: 1168. Thesis (Ph.D.)--University of Windsor (Canada), 1988.

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