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Computational Analysis of Stereospecificity in the Cope Rearrangement
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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.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Computer-Based LearningKeywords (Subject):
AlkenesCiting Articles
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
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- Received: August 03, 2009
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