Diastereomeric transition states. Relative energies of the chair and boat reaction pathways in the Cope rearrangement
KJ Shea, RB Phillips
Index: Shea, Kenneth J.; Phillips, Richard B. Journal of the American Chemical Society, 1980 , vol. 102, # 9 p. 3156 - 3162
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Citation Number: 34
Abstract
Abstract: Thermal rearrangement of dl-and meso-2, 2'-bismethylenecyclopentane and 2, 2'- bismethylenecyclohexane is re-ported. The rates of rearrangement permit independent measurement of the high-and low-energy conformations of the Cope rearrangement. The transition-state geometry for each diastereomer is uniquely defined as Czl,(boat) for the meso isomer and C2h (chair) for the dl diastereomer. Correlation of these findings with ...
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