The two naturally occurring cyclopropene fatty acids, sterculic and malvalic, have been synthesized. The cyclopropene ring was made by inserting a methylene unit into an acetylenic linkage. The synthesis of methyl sterculate was repeated using diethyl aluminum chloride, diazomethane, and methyl stearolate. Methyl malvalate was totally synthesized. Diethyl malonate was condensed with 1, 5-dibromopentane to give 7-bromoheptanoic acid. 1-Decyne was reacted with 7-bromoheptanoic acid to give 7-heptadecynoic acid. 7-Heptadecynoic acid was esterified with diazomethane. The cyclopropene ring was generated using diethyl aluminum chloride and diazomethane. The reaction worked very well and in most cases the yields exceeded 50 percent. / Graduation date: 1966

M.Sc. (Chemistry) / Please refer to full text to view abstract

Kwok Ka-chu. / Thesis (M.Phil.)--Chinese University of Hong Kong. / Bibliography: leaves 53-56.

Thesis (M.Phil.)--Chinese University of Hong Kong. / Bibliography: leaves 59-62.

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Shen, Hao. / "July 2007." / n and 0 in "4fn/d0" in title is superscript. / Thesis (Ph.D.)--Chinese University of Hong Kong, 2007. / Includes bibliographical references (p. 207-220). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstracts in English and Chinese.

A series of salts of the strong fluorocarbon acid bis(trifluoromethylsulfonyl)methane were made: (CF3S02 ) 2CHK, (CF3S02 ) 2CHLi, [ (CF3S02 ) 2CH] 2Ca, [ (CF3S02 ) 2CH] 2Hg, (CF3S02 ) 2CHAg, [ (CF3S02 ) 2CH] 3La. Their reactivity and use as organic intermediates were investigated. The salts were made from their corresponding carbonates, oxides, or hydrides. The reaction times for the salts is generally short, however the purification process was laborious, involving recrystallization from organic solvents and drying under vacuum. The lithium salt is being evaluated as a solid state battery electrolyte. Derivatives of bis(trifluoromethylsulfonyl)methane were made by using the salts as nucleophiles in organic reactions. Reactions with Br2 , CH2=CH2CH2Br, CH3CH2CH2I, and OCH2CHCH2Br were carried out to make: bis(trifluormethylsulfonyl)bromomethane, 4,4-bis(trifluormethylsulfonyl)butene-1, 1,1-bis(trifluormethylsulfonyl)butane, and 4,4-bis(trifluormethylsulfonyl)-1,3-epoxybutane In addition, work was carried out on the synthesis of the polymer -(-O-CH2-C(CH20CF2CF2S02F)H-)n- and the corresponding lithium salt. The polymer was treated with aqueous lithium hydroxide in order to convert the S02F group to a S03-Li+ group. This salt is being investigated as a solid state ion conducting polymer. All products were characterized by infrared spectroscopy, mass spectroscopy, 1H and 19F nuclear magnetic resonance spectroscopy, elemental analysis, and melting points.

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Graduation date: 1991