Synthesis of S,S,O-orthoesters and 1,1-difluoroalkyl ethers via reaction of peroxides with lithiated 1,3-dithianes

Shiva Kumar Kyasa, Patrick H. Dussault

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Alkyl tetrahydropyranyl peroxides (ROOTHP) transfer alkoxide (OR) to lithiated 1,3-dithianes. The derived S,S,O-orthoesters undergo fluorodesulfurization with HF/pyridine and N-bromosuccinamide (NBS) to furnish difluoromethyl ethers. The overall protocol can be applied to synthesis of both terminal (ROCF2H) and internal (ROCF2R′) ethers. Application of the same set of reactions to a lithiated tris(alkylthio)alkane is shown to generate a trifluoromethyl ether. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)5235-5237
Number of pages3
JournalOrganic Letters
Volume16
Issue number20
DOIs
StatePublished - Oct 17 2014

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Ethers
Peroxides
peroxides
ethers
Alkanes
synthesis
Ether
alkoxides
alkanes
pyridines
1,3-dithiane
caN protocol
pyridine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis of S,S,O-orthoesters and 1,1-difluoroalkyl ethers via reaction of peroxides with lithiated 1,3-dithianes. / Kyasa, Shiva Kumar; Dussault, Patrick H.

In: Organic Letters, Vol. 16, No. 20, 17.10.2014, p. 5235-5237.

Research output: Contribution to journalArticle

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