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Regio- and Stereoselectivity of Water Elimination as a Function of Ring Size
1Institut für Pharmazeutische Chemie der Philipps-Universität, Marbacher Weg 6, 35032 Marburg, Germany.
The Journal of Organic Chemistry
|October 24, 2001
Abstract:
The elimination of water from tertiary alcohols was studied for carbocycles of ring size 5-16. The resulting olefins 3-5 were discriminated by NMR spectroscopy. The relative amount of their formation reflects the steric idiosyncrasies of the respective ring systems. The behavior of the medium-sized rings yielded experimental proof to the I-strain concept.