The generation and fate of strained, unsaturated, bicyclic hydrocarbons
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The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
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The Department of Chemistry was founded in 1880.
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1880-present
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- College of Liberal Arts and Sciences (parent college)
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Abstract
Bicyclo (2.2.2) oct-1-ene 1 was generated by gas phase elimination of trimethylsilyl bromide from 1-bromo-2-(trimethylsilyl)-bicyclo (2.2.2) octane (2). The elimination was effected by passing vapors of 2 over solid-supported tetra-n-butyl ammonium fluoride at room temperature and reduced pressure. Three dimers of 1 were identified by their X-ray crystal structures. A pair of diastereomeric, head-to-head dimers, along with the previously known head-to-tail dimer demonstrate the non-ionic character of the Bredt olefin 1. Attempts to generate bicyclo (2.2.2) octa-1,2-diene are reported;Bicycloalkylidene carbenes are generated in the gas phase and in solution. Factors influencing the fate of these species are discussed. Force field calculations of a series of cyclic and bicyclic vinylidenes are reported and analyzed in the context of ring expansion versus ring contraction. Attempts to synthesize a low temperature, thermal precursor to bicyclic vinylidene are discussed.