R. S. Monson
1971
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Abstract
Publisher Summary This chapter presents the feature of structural isomerizations. Structural isomerizations incorporate a variety of reagents and procedures from acid catalysts to photolysis. The rearrangement of certain saturated hydrocarbons under the influence of Lewis acids has been known for some time. Cyclohexane, for example, is converted into a mixture of hydrocarbons including methylcyclopentane. The chapter describes that the readily prepared 1-ethynylcyclohexanol can be isomerized with acidic catalysts into 1-acetylcyclohexene, a compound of considerable use in the building up of polycyclic molecules. The chapter presents Schleyer's synthesis as well as a modification wherein the product is isolated by a thiourea inclusion complex. Photolytic reactions of dienes frequently give complex mixtures of rearranged products. Certain β-diketones react in the presence of hydrogen peroxide to give rearranged carboxylic acids. The chapter explains that the treatment of 1, 1-dihalocyclopropanes by methyllithium is a general route to allenes, in the condition that the product is not highly strained.