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 C2 propeller conformation in solution and the enantiomerization process occurs with ΔG≠ = 20.0 kcal mol-1 for I and ΔG≠ = 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. © 1990.
Static and dynamic stereochemistry of ortho-bridged diarylsulphones / Finocchiaro, P.; Bonsignore, F.; Libertini, E.; Newton, A. B.; Clark, D. T.. - In: JOURNAL OF MOLECULAR STRUCTURE. - ISSN 0022-2860. - 238:C(1990), pp. 307-313. [10.1016/0022-2860(90)85022-B]
Static and dynamic stereochemistry of ortho-bridged diarylsulphones
Libertini E.;
1990
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 C2 propeller conformation in solution and the enantiomerization process occurs with ΔG≠ = 20.0 kcal mol-1 for I and ΔG≠ = 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. © 1990.
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