Ultrasound promoted hypervalent iodine reactions: (α-tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene

Atilla Tuncay, John A. Dustman, George Fisher, Crystal I. Tuncay, Kenneth S. Suslick

Research output: Contribution to journalArticlepeer-review

Abstract

Ultrasound enhances substantially the rates of α-tosyloxylation of ketones with [hydroxy(tosyloxy)iodo] benzene and thus provides a direct, quick, and mild method of tosyloxylation of ketones without the generation of time-consuming intermediates such as trimethylsilyl enol ether derivatives and α-hydroxy ketones. The present method also provides convenient access to the tosylates of alicyclic ketones such as cyclopentanone and cycloheptanone which are otherwise very difficult to obtain.

Original languageEnglish (US)
Pages (from-to)7647-7650
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number50
DOIs
StatePublished - Dec 8 1993

Keywords

  • hypervalent iodine
  • sonochemistry
  • ultrasound
  • α-tosyloxylation of ketones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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