Steroid dialkylcarbene reactions Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/k643b4966

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  • Steroid carbenes have been investigated as synthetic intermediates. Basic decomposition of 4-en-3-one tosylhydrazones (and other A-ring systems) gives varying amounts of 2, 4-dienes, and solvent derived products with diglyme, heptane, tetrachloroethylene, carbon tetrachloride, benzene and cyclohexene. A method for separating complex product mixtures was developed and a study of the effect of reaction conditions carried out. Butyl lithium decomposition gives a high yield of the homoannular diene. Sterically hindered carbenes give only intramolecular products. Saturated steroid carbenes have been shown to give widely varying γ/β insertion ratios. Decomposition of cholestan-3-one tosylhydrazone in tetrachloroethylene results in the formation of a solvent derieved pyrazoline. The possible role of pyrazolines in other carbene reactions is discussed, A facile route to interesting fused ring pyrazoles has been developed in the l6-en-20-one tosylhydrazone system. With a 16-methyl system the pyrazolenine was isolated and investigated. The 'possible biological properties of these compounds are discussed.
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  • description.provenance : Approved for entry into archive by Patricia Black(patricia.black@oregonstate.edu) on 2014-03-12T21:05:16Z (GMT) No. of bitstreams: 1 DixonDaleD1968.pdf: 2051053 bytes, checksum: 38da0528b3d0b5149fd4b5c162227f0b (MD5)
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  • description.provenance : Made available in DSpace on 2014-03-13T17:21:24Z (GMT). No. of bitstreams: 1 DixonDaleD1968.pdf: 2051053 bytes, checksum: 38da0528b3d0b5149fd4b5c162227f0b (MD5) Previous issue date: 1968-05-14

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