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Diaryldiacyloxyspirosulfuranes. Part 3. Sulfuranes with Five-, Six- and Seven-membered Spirorings: Syntheses and Molecular Structures

DOI: 10.1039/P29930000847

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 847 - 853 (1993)

Update date:2022-08-16

Topics:

Authors:

Kapovits, IstvanKapovits, Istvan

Rabai, JozsefRabai, Jozsef

Szabo, DenesSzabo, Denes

Czako, KlaraCzako, Klara

Kucsman, ArpadKucsman, Arpad

et al.et al.

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Article abstract of DOI:10.1039/P29930000847

Three novel diaryldiacyloxyspirosulfuranes (2-4) with five-, six- and seven-membered spirorings have been prepared, and their molecular structures determined by X-ray diffraction.The structure of spirosulfurane 1 with two identical five-membered spirorings has been reinvestigated.In all spirosulfuranes 1-4 the arrangement of the ligands about the central sulfur atom show a slightly distorted trigonal bipyramidal (TBP) geometry resulting in chiral molecular structure.The axial (hypervalent) S-O and equatorial (covalent) S-Car bond lengths range from 1.838(1) to 1.872(3) and from 1.771(3) to 1.794(4) Angstroem, respectively.The axial O-S-O and equatorial Car-S-Car bond angles lie in the narrow intervals of 174.9(2)-177.4(4) deg and 105.8(2)-106.9(2) deg, respectively.The five-membered spirorings are practically planar in 1-3.The six-membered spirorings in 2 and 4 assume distorted sofa conformations.The seven-membered spiroring in 3, having four Car atoms with planar configuration, is irregular.The aromatic rings fused with the spirorings are perpendicular to the equatorial plane only if the spiroring is five-membered.In other cases the stable conformations with TBP geometry about sulfur involve a significant torsion of the aromatic ring about the S-Car axis.Thus, in diaryldiacyloxyspirosulfuranes having acyloxy-O ligands at axial positions the structural parameters about the sulfur are not considerably influenced by the shape and size of the spirorings.The O-S-O moiety with hypervalent bonds may be regarded as a structural unity.The sum of the individual S-O bond lengths, (3.684-3.744 Angstroem) which is characteristic of diaryldiacyloxyspirosufuranes, differs markedly from the values found earlier for dialkoxy- and acyloxy-alkyloxy analogues (3.601 and 3.910 Angstroem, respectively).For spirosulfurane 3 a rearrangement into the isomeric ten-membered cyclic anhydride 13 is observed.

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