Regio- and Stereoselectivity of Water Elimination as a Function of Ring Size.
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.
Greve
Björn
B
Institut für Pharmazeutische Chemie der Philipps-Universität, Marbacher Weg 6, 35032 Marburg, Germany.
Imming
Peter
P