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Synthesis, Enantiomeric Conformations, and Stereodynamics of Aromatic ortho-Substituted Disulfones

Published in Helvetica chimica acta. 2003, vol. 86, no. 1, p. 65-81
Abstract 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 (? and d) as evidenced by 31P- and 1H-NMR data of the chiral D3-symmetric tris{4,5-bis[(4-methylphenyl)sulfonyl]benzene-1,2-diolato(2-)-?O,?O}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-yl]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 1H-NMR in the temperature range of 110°, the corresponding free energy being 19.8 kcalmol-1.
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LACOUR, Jérôme et al. Synthesis, Enantiomeric Conformations, and Stereodynamics of Aromatic ortho-Substituted Disulfones. In: Helvetica chimica acta, 2003, vol. 86, n° 1, p. 65-81. doi: 10.1002/hlca.200390020 https://archive-ouverte.unige.ch/unige:7832

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Deposited on : 2010-06-21

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