Base-promoted Epoxide Isomerization
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Base-promoted Epoxide Isomerization
Base-promoted epoxide isomerization is the conversion of Alkane, alkyl epoxides to Cyclic compound#Ring-closing & opening reactions, ring-opened products through the action of strong Base (chemistry), base. Isomerizations of this type are most often used to synthesize allylic alcohols, although other products are possible. Introduction In the presence of lithium or aluminum amide bases, epoxides may open to give the corresponding allylic alcohols. Removal of a proton adjacent to the epoxide, elimination, and neutralization of the resulting alkoxide lead to synthetically useful allylic alcohol products. In reactions of chiral, non-racemic epoxides, the configuration of the allylic alcohol product matches that of the epoxide substrate at the carbon whose C–O bond does not break (the starred carbon below). Besides Dehydrohalogenation, β-elimination some other reactions are possible, as metalation of the epoxide ring can take place competitively. Vinylogy, Vinylogous eliminations ar ...
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Alkane
In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula . The alkanes range in complexity from the simplest case of methane (), where ''n'' = 1 (sometimes called the parent molecule), to arbitrarily large and complex molecules, like pentacontane () or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane (). The International Union of Pure and Applied Chemistry (IUPAC) defines alkanes as "acyclic branched or unbranched hydrocarbons having the general formula , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms". However, some sources use the term to denote ''any'' saturated hydrocarbon, including those that are either monocyclic (i.e. the cycloalkanes) or ...
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