1H, 13C, 17O NMR and quantum-chemical study of the stereochemistry of the sulfoxide and sulfone derivatives of 3-arylidene-1-thioflavan-4-one epoxides
作者： József Kovács , Gábor Tóth , András Simon , Albert Lévai , Andreas Koch
DOI: 10.1002/MRC.1153
关键词:
摘要: The oxidation of the trans,cis-(2) and trans,trans-epoxides (3) differently substituted (Z)-3-arylidene-1-thioflavan-4-ones (1) with dimethyldioxirane (DMD) yielded appropriate sulfoxides (4, 5) sulfones (6, 7). structures were elucidated by extensive application one- two-dimensional 1H, 13C 17O NMR spectroscopy. conformational analysis was achieved 3J(C,H) coupling constants, NOESY responses ab initio calculations. preferred ground-state conformers (twisted envelope-A, twisted envelope-B for 6 7) obtained as global minima theoretical MO study also examination chemical shifts, calculated sulfone isomers GIAO method. Analogous results, sulfoxide 5), not only led to but gave evidence trans arrangement 2-Ph group oxygen atom SO group. Chemical shift differences between isomers, corroborated calculations anisotropic effects oxirane ring SO2 groups. Copyright © 2003 John Wiley & Sons, Ltd.
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