Memorial University DAI: Investigations into the intramolecular geminal acylation reaction

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Document Description

Title	Investigations into the intramolecular geminal acylation reaction
Author	Blanchard, Angela N., 1976-
Description	Thesis (M.Sc.)--Memorial University of Newfoundland, 2000. Chemistry
Date	2000
Pagination	vii, 138 leaves : ill.
Subject	Acylation; Carbonyl compounds
Degree	M.Sc.
Degree Grantor	Memorial University of Newfoundland. Dept. of Chemistry
Discipline	Chemistry
Language	eng
Notes	Bibliography: leaves 81-83
Abstract	The geminal acylation reaction, initially introduced by Kuwajima and co-workers, has been developed into a synthetically useful method of creating cyclic diketones by reacting l, 2-bis[(trimethylsilyl)oxy]cyclobutene (1) with aldehydes, ketones, or acetals. To date, all examples of the reaction are intermolecular. The focus of this research was to develop methodology for an intramolecular geminal acylation. This process would lead to bridged compounds with two carbonyl functionalities. -- Compounds that should be capable of performing an intramolecular germinal acylation have been synthesized. These compounds possess a reactive functionality similar to that of 1, and an acetal moiety. Attempts at performing this reaction have been made and the results are quite promising. Several bridged diketones have been generated. There have been other compounds isolated that indicate that this reaction does proceed, however isolating the desired products has been problematic due to destruction of the bridged diketones within the reaction mixture.
Type	Text
Resource Type	Electronic thesis or dissertation
Format	Image/jpeg; Application/pdf
Source	Paper copy kept in the Centre for Newfoundland Studies, Memorial University Libraries
Local Identifier	a1492110
Rights	The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission.
Collection	Electronic Theses and Dissertations
Scanning Status	Completed
PDF File	(28.22 MB) -- http://collections.mun.ca/PDFs/theses/Blanchard_AngelaN.pdf
CONTENTdm file name	66520.cpd