Computational Analysis of Stereospecificity in the Cope Rearrangement.

• Autores: Laura Glish, Timothy W. Hanks
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 84, Nº 12, 2007, págs. 2001-2003
• Idioma: inglés
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• Resumen

  • The Cope rearrangement is a highly stereospecific, concerted reaction of considerable synthetic utility. Experimental product distributions from the reaction of disubstituted 1,5-hexadienes can be readily understood by computer modeling of the various possible transitions states. Semi-empirical methods give relative energies of transition states that parallel those of more sophisticated methods at a fraction of the computational time. Visual analysis of computed transition-state geometries allow students to interpret the computational results by analogy to the familiar chair and boat conformations of substituted cyclohexanes.