Abstract

Ortho-bridged diarylsulphones I and II have been synthesized and their static and dynamic stereochemistry has been investigated by variable temperature 1H NMR spectroscopy. The results indicate that both compounds adopt a C 2 propeller conformation in solution and the enantiomerization process occurs with Δ G ≠ = 20.0 kcal mol −1 for I and Δ G ≠ = 18.15 kcal mol −1 for II. The mechanism leading to the stereoisomerization process is believed to occur through a two-ring flip transition state.

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