Synthesis, enantiomeric conformations, and stereodynamics of aromatic ortho-substituted disulfones.
[structure in text] Aromatic ortho-disulfone derivatives are readily accessible from diiodide precursors by Cu(I)-mediated reactions with sodium sulfinate salts. The sulfone substituents adopt C(2)-symmetric enantiomeric conformations (lambda and delta) as evidenced by X-ray structural analysis and (1)H and (31)P NMR on chiral bis(sulfonyl)veratrol derivatives and hexacoordinated tris(benzenediolato)phosphate anions. Slow dynamic conformational isomerism (DeltaG(++) > or = 19.8 kcal mol(-1)) was detected in solution.
Lacour
J
J
Département de Chimie Organique, Université de Genève, quai Ernest-Ansermet 30, CH-1211 Genève 4, Switzerland. jerome.lacour@chiorg.unige.ch
Monchaud
D
D
Bernardinelli
G
G
Favarger
F
F