Title

Computational Analysis of Stereospecificity in the Cope Rearrangement

ACS Citation

Glish, L.; Hanks, T. W. Computational Analysis of Stereospecificity in the Cope Rearrangement. J. Chem. Educ. 2007, 84, 2001-2001.

Abstract

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. 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.

Source Name

Journal of Chemical Education

Publication Date

1-1-2007

Volume

84

Issue

12

Page(s)

165-175

Document Type

Citation

Citation Type

Article