Synthesis, enantiomeric conformations, and stereodynamics of aromatic ortho-substituted disulfones

J Lacour; D Monchaud; G Bernardinelli; F Favarger

doi:10.1021/ol015804d

Synthesis, enantiomeric conformations, and stereodynamics of aromatic ortho-substituted disulfones

Org Lett. 2001 May 3;3(9):1407-10. doi: 10.1021/ol015804d.

Authors

J Lacour¹, D Monchaud, G Bernardinelli, F Favarger

Affiliation

¹ Département de Chimie Organique, Université de Genève, quai Ernest-Ansermet 30, CH-1211 Genève 4, Switzerland. [email protected]

PMID: 11348246
DOI: 10.1021/ol015804d

Abstract

[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.