Thermal disrotatory electrocyclic isomerization of cis-bicyclo[4.2.0]oct-7-ene to cis,cis-1,3-cyclooctadiene |
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Authors: | Baldwin John E Gallagher Sarah S Leber Phyllis A Raghavan Anuradha |
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Institution: | Department of Chemistry, Syracuse University, Syracuse, New York 13244, USA. jbaldwin@syr.edu |
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Abstract: | reaction: see text] The ratio of observed rate constants, k/k', for thermal isomerizations of cis-bicyclo4.2.0]oct-7-ene and its 2,2,5,5-d(4) analogue to cis,cis-1,3-cyclooctadienes at 250 degrees C is 1.17, indicative of a secondary, not a primary, deuterium kinetic isotope effect. The reaction does not occur through a 1,5] hydrogen shift from the transient cis,trans-1,3-cyclooctadiene intermediate to form the observed cis,cis-diene product. |
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