Some reactions of 6-ketocholestanyl acetate
| dc.contributor.author | Wallis, A. F. A. | en |
| dc.date.accessioned | 2014-02-25T19:48:39Z | |
| dc.date.available | 2014-02-25T19:48:39Z | |
| dc.date.issued | 1962 | en |
| dc.description.abstract | Enol acetylation of 6-ketocholestanyl acetate by acetic anhydride-sulphuric acid or acetic anhydride-perchloric acid gave the Δ⁵-enol acetate, which on bromination yielded the known 5α-bromo-ketone. Isopropenyl acetate enol acetylation afforded a 1:1 mixture of Δ⁵ - and Δ⁶-isomers, the ratio being determined by bromination of the enol acetate mixture followed by O.R.D. and specific rotation measurements on the mixed 5α- and 7α-bromo-ketone. The 7α-bromo-ketone with pyridine-silver nitrate gave the known 3β-acetoxy-cholesta-6,7-dione together with the 6-keto-Δ⁷-ketone. Dehydrobromination of the 7α-bromo compound by N,N-dimethyl formamide-lithium carbonate gave the 6-keto-Δ-compound in good yield. From O.R.D. measurements the structure of the enol form of 3α-acetoxy-cholesta-6,7-dione has been assigned. A preliminary study has been made of the enol acetylation of both 3βacetoxy-7α-bromo-cholestan-6-one and 3β-acetoxy-cholest-4-en-6-one.dcvalue> | en |
| dc.identifier.uri | http://hdl.handle.net/10092/8895 | |
| dc.identifier.uri | http://dx.doi.org/10.26021/6805 | |
| dc.language.iso | en | |
| dc.publisher | University of Canterbury. Chemistry | en |
| dc.relation.isreferencedby | NZCU | en |
| dc.rights | Copyright A. F. A. Wallis | en |
| dc.rights.uri | https://canterbury.libguides.com/rights/theses | en |
| dc.title | Some reactions of 6-ketocholestanyl acetate | en |
| dc.type | Theses / Dissertations | |
| thesis.degree.discipline | Chemistry | en |
| thesis.degree.grantor | University of Canterbury | en |
| thesis.degree.level | Masters | en |
| thesis.degree.name | Master of Science | en |
| uc.bibnumber | 348674 | en |
| uc.college | Faculty of Science | en |
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