344958-59-4Relevant academic research and scientific papers
Synthesis, enantiomeric conformations, and stereodynamics of aromatic orffto-substituted disulfones
Lacour, Jerome,Monchaud, David,Bernardinelli, Gerald,Favarger, France
, p. 1407 - 1410 (2001)
(equation presented) Aromatic ortho-disulfone derivatives are readily accessible from diiodide precursors by Cu(l)-mediated reactions with sodium sulfinate salts. The sulfone substituents adopt C2-symmetric enantiomeric conformations (λ and δ)
Synthesis, enantiomeric conformations, and stereodynamics of aromatic ortho-substituted disulfones
Lacour, Jerome,Monchaud, David,Mareda, Jiri,Favarger, France,Bernardinelli, Gerald
, p. 65 - 81 (2007/10/03)
Aromatic ortho-disulfone derivatives are readily accessible from diiodide precursors by CuI-mediated reaction with sodium sulfinate salts (DMF, 110°). The sulfonyl substituents adopt in solution and in the solid state two enantiomeric conformations (λ and δ) as evidenced by 31P- and IH-NMR data of the chiral D3-symmetric tris{4,5-bis[(4-methylphenyl)sulfonyl]benzene-1,2-diolato(2-)- κO,κO′}phosphate(v) anion (3a) and 1,2-bis(camphor-10-sulfonyl)-4,5-dimethoxybenzene((=1, 2-bis{{[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]- hept-1-y1]methyl}sulfonyl}-4,5-dimethoxybenzene; 6c). X-Ray structure analysis of 1,2-dimethoxy-4,5-bis(methylsulfonyl)benzene (6a) and 1,2-dimethoxy-4,5-bis(4-methylphenyl)sulfonyl]benzene (6b) confirmed in the solid state the preferred chiral orientation of the sulfonyl groups. Dynamic conformational isomerism was detected for 6c in its IH-NMR in the temperature range of 110°, the corresponding free energy being 19.8 kcal mol-1.
