Hexitol derivatives containing a 1,4-oxathiane ring-III. Rearrangement of a sulfone on treatment with LAH

J. Kuszmann, P. Sohár, Gy Horváth, Zs Méhesfalvi-Vajna

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Abstract

Treatment of 2,5 - anhydro - 3,4 - di -O- mesyl - 1,6 - thioanhydro - D - glucitol S,S-dioxide (1) with LAH afforded (1S,6R)-2-thiabicyclo[4.1.0]heptane S,S-dioxide (2) and its (4R) - 4 -hydroxy derivative 3 in a ratio of 46:6. Sodium - dihydro - bis(2 - methoxy - ethoxy) - aluminate afforded the same compounds in a ratio of 15:22. The corresponding sulfide 5 underwent no rearrangement under similar conditions. The structure of the products was established by IR, PMR, CMR and MS. A probable reaction mechanism is discussed.

Original languageEnglish
Pages (from-to)3905-3910
Number of pages6
JournalTetrahedron
Volume30
Issue number21
DOIs
Publication statusPublished - 1974

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Heptanes
Sulfones
Sorbitol
Sulfides
Sodium
Derivatives
hexitol
oxathiane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Hexitol derivatives containing a 1,4-oxathiane ring-III. Rearrangement of a sulfone on treatment with LAH. / Kuszmann, J.; Sohár, P.; Horváth, Gy; Méhesfalvi-Vajna, Zs.

In: Tetrahedron, Vol. 30, No. 21, 1974, p. 3905-3910.

Research output: Contribution to journalArticle

Kuszmann, J. ; Sohár, P. ; Horváth, Gy ; Méhesfalvi-Vajna, Zs. / Hexitol derivatives containing a 1,4-oxathiane ring-III. Rearrangement of a sulfone on treatment with LAH. In: Tetrahedron. 1974 ; Vol. 30, No. 21. pp. 3905-3910.
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AU - Méhesfalvi-Vajna, Zs

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