Diaryldiacyloxyspirosulfuranes-II. Syntheses from sulfoxides and hydrolysis

I. Kapovits, J. Rábai, F. Ruff, Á Kucsman, B. Tanács

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The preparations of spirocyclic sulfuranes from bis(2-carboxyaryl) sulfoxides with dehydrating agents were investigated. Depending on the manner of dehydration, spirosulfurane formation follows different courses established by using 18O-labelled 2,2'-sulfinyldibenzoic acid. Sulfoxides with 2-carboxybenzyl group failing to form spirosulfuranes undergo the Pummerer reaction yielding lactones. In aqueous dioxan spirosulfuranes hydrolyse generally into sulfoxides. A spirosulfurane having two nitro groups on the same aromatic ring hydrolyses with S-Car bond cleavage.

Original languageEnglish
Pages (from-to)1875-1881
Number of pages7
JournalTetrahedron
Volume35
Issue number15
DOIs
Publication statusPublished - 1979

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Sulfoxides
Hydrolysis
Lactones
Dehydration
Railroad cars
Acids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Diaryldiacyloxyspirosulfuranes-II. Syntheses from sulfoxides and hydrolysis. / Kapovits, I.; Rábai, J.; Ruff, F.; Kucsman, Á; Tanács, B.

In: Tetrahedron, Vol. 35, No. 15, 1979, p. 1875-1881.

Research output: Contribution to journalArticle

Kapovits, I. ; Rábai, J. ; Ruff, F. ; Kucsman, Á ; Tanács, B. / Diaryldiacyloxyspirosulfuranes-II. Syntheses from sulfoxides and hydrolysis. In: Tetrahedron. 1979 ; Vol. 35, No. 15. pp. 1875-1881.
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