Abstract
AbstractPlanar chiral (arene)Cr(CO)3‐substituted propargyl cations can be diastereoselectively generated from propargyl acetates with the use of strong Lewis acids, and they have been structurally characterized by UV/Vis and 13C NMR spectroscopy. At low temperatures (<–65 °C) the s‐cis isomer is exclusively obtained as a product of a kinetically controlled ionization. DFT studies on the structure of the propargyl cations and on the Cipso–Cα bond rotation to give the thermodynamically favored s‐trans isomer reveal that the substitution pattern at the γ‐propargyl position has a stronger impact on the height of the rotational barrier than the substituent on the complexed aryl ring. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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