Mechanism and application of the Newman-Kwart O -> S rearrangement of O-aryl thiocarbamates

Guy C. Lloyd-Jones*, Jonathan D. Moseley, Joseph S. Renny

*Corresponding author for this work

Research output: Contribution to journalLiterature reviewpeer-review

Abstract

This literature review focuses on the thermal rearrangement of O-aryl thiocarbamates to yield the corresponding S-aryl thiocarbamates: the Newman-Kwart rearrangement. The purpose of the review is to highlight the utility of the rearrangement which provides a key step in an efficient route to convert phenols into thiophenols. The scope of the Newman-Kwart rearrangement is illustrated by way of numerous examples of its application to the preparation of Ar-S species ranging from large-scale industrial processes through to the synthesis of complex organic molecules such as ligands and supramolecular structures. The review contains 238 references and covers just over 40 years of the literature, from the first reports of the rearrangement by Edwards and Pianka in 1965 up to mid-2007.

Original languageEnglish
Pages (from-to)661-689
Number of pages29
JournalSynthesis: Journal of Synthetic Organic Chemistry
Issue number5
DOIs
Publication statusPublished - 3 Mar 2008

Keywords

  • Newman-Kwart
  • aryl thiocarbamates
  • aryl thiols
  • thermal rearrangement
  • mechanism
  • NONSTEROIDAL ANTIINFLAMMATORY AGENTS
  • POTENTIAL PHOTOBIOLOGICAL ACTIVITY
  • AXIALLY CHIRAL P,S-HETERODONOR
  • ALDOSE REDUCTASE INHIBITORS
  • SULFUR-CONTAINING POLYMERS
  • THIA-FRIES REARRANGEMENT
  • STERIC RATE ENHANCEMENT
  • ASYMMETRIC CATALYSIS
  • CONJUGATE ADDITION
  • ACID-DERIVATIVES

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