The structure of a spirosulfurane rearrangement product: X-ray study of a ten-membered cyclic acid anhydride

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Abstract

The structure of the cyclic anhydride product 2 (2,5,10-trioxo-tribenzo[c, f, h]-1,5-oxathiecine) obtained from the spirosulfurane 1 with five- and seven-membered spirorings (3H-2,1-benzoxathiole-1-spiro-1′-(3H-dibenzo[c,e]-2,1-oxathiepine)-3,3′-dione) by heating in dry pyridine [I. Kapovits, J. Rábai, D. Szabó, K. Czakó, Á. Kucsman, Gy. Argay, V. Fülöp, A. Kálmán, T. Koritsánszky and L. Párkányi, J. Chem. Soc., Perkin Trans. 2, (1993) 847] has been established by X-ray crystallography from diffractometer data. Compound 2 with unaltered brutto chemical formula (C20H12O4S) crystallizes in the monoclinic space group P21/n (No. 14) with a = 7.268(1), b = 16.132(1), c = 13.308(1) Å, β = 101.18(1)°, V = 1530.7(2) Å3, Z = 4, Dc = 1.512g cm-3 and μ(Cu-Kα) = 19.6 cm-1. The structure has been solved by direct methods and refined to R = 0.049 for 2598 observed reflections. The rearrangement of the spirosulfurane 1 yields a ten-membered ring closed by the newly formed anhydride moiety. The anhydride ring is crosslinked by an S ⋯ O close contact (2.661(1) Å) formed from one of the SO hypervalent bonds, while the second hypervalent bond (S → O = 1.862(3) Å) is replaced by the double bond (1.489(1) Å) of a sulfoxide group. The OS⋯O angle remains close to 180°. The ten-membered ring is divided by the through-space S ⋯ O interaction into a seven- and a five-membered ring. Their similarity to the corresponding seven- and five-membered rings of the spirosulfurane are discussed.

Original languageEnglish
Pages (from-to)279-285
Number of pages7
JournalJournal of Molecular Structure
Volume317
Issue number3
DOIs
Publication statusPublished - Feb 10 1994

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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