Oxidative rearrangements of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95% methanol: A general, regiospecific synthesis of α-aryl ketones

Michael W. Justik, Gerald F. Koser

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63 Citations (Scopus)

Abstract

The treatment of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95% methanol affords the corresponding α-aryl ketones. This oxidative rearrangement is general for acyclic and cyclic arylalkenes and permits regioselective syntheses of isomeric α-phenyl ketone pairs.

Original languageEnglish (US)
Pages (from-to)6159-6163
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number32
DOIs
StatePublished - Aug 2 2004

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Ketones
Methanol
(hydroxy(tosyloxy)iodo)benzene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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title = "Oxidative rearrangements of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95{\%} methanol: A general, regiospecific synthesis of α-aryl ketones",
abstract = "The treatment of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95{\%} methanol affords the corresponding α-aryl ketones. This oxidative rearrangement is general for acyclic and cyclic arylalkenes and permits regioselective syntheses of isomeric α-phenyl ketone pairs.",
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AB - The treatment of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95% methanol affords the corresponding α-aryl ketones. This oxidative rearrangement is general for acyclic and cyclic arylalkenes and permits regioselective syntheses of isomeric α-phenyl ketone pairs.

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