3 resultados para S(N)2 lactone ring opening

em Brock University, Canada


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This research work has been planned with the intention of proving the absolute configuration of lactobacillc acid. During the course of this work, attempts have been made to synthesize cis-2-carboxycyclopropane- l-.acetic acid as,v,a suitable resolvable material. As the results were not satisfactory, the synthesis of ci,s-2-carboxycyclopropane-l-propionic acid has been alternatively attempted by ring opening of bicyclo- [4.1.~-heptan-2-onewithout much success. Attempts to resolve or prepare bicyclo[ 4.1.~-hePtan-2-one optically active are also reported. On the other hand, a complete scheme is described for the possible synthesis of optically active lactobacillic acid. If only bicyclo- ~.1.~ -heptan-2-one can be resolved or prepared optically active, this described scheme can be applied smoothly to the synthesis of enant~omeric lactobacillic acid.

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The Canadian Niagara Power Company was created in 1892, in large part due to the efforts of William Birch Rankine, a businessman who pioneered the development of hydropower on both the Canadian and American shores of the Niagara River. Numerous delays and problems postponed the construction and operation of the company's powerhouse, which was formally opened on January 2, 1905. Upon opening, the powerhouse boasted the largest generators of their kind in the world, with a capacity of 10,000 electrical horsepower each. The company was acquired by FortisOntario in 2002. In 2009, the company’s water rights expired and the Canadian Niagara Powerhouse building, also known as the Rankine Generating Station, was turned over to the Niagara Parks Commission.

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The first example of a [5+2] cycloaddition reaction wherein the olefin of the vinylcyclopropyl moiety is constrained in a carbocycle was explored, and possible reasons on the lack of reactivity of the substrate were studied. A simple model substrate was synthesized and subjected to cycloaddition conditions to determine if the reason for the lack of reactivity was related to the complexity of the substrate, or if the lack of “conjugative character” of the cyclopropyl ring with respect to the olefin is responsible. A more complex bicyclic substrate possessing an angular methyl group at the ring junction was also synthesized and explored, with evidence supporting the current theory of deconjugation of the cyclopropyl moiety.