Sulfur-Mediated Rearrangements II pp 131-161

Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 275)

Thione–Thiol Rearrangement: Miyazaki–Newman–Kwart Rearrangement and Others

  • Cristiano Zonta
  • Ottorino De Lucchi
  • Raffaella Volpicelli
  • Livius Cotarca

Abstract

Thione-to-thiol rearrangements represent a general route for the synthesis of sulfur compoundsfrom hydroxyl functionalities. In particular, the Miyazaki–Newman–Kwart rearrangementhas been widely used for the synthesis of aromatic thiols from the corresponding phenols.

Thermal rearrangement Newman–Kwart rearrangement Aromatic thiols 

Abbreviations

DMF

Dimethylformamide

DABCO

1,4-Diazabiciclo[2.2.2]octane

DMAP

Dimethylaminopyridine

DMTCl

Dimethylthiocarbamoyl chloride

DETCl

Diethylthiocarbamoyl chloride

PTC

Phase transfer catalyst

BINOL

Binaphthol

MOP

2-(Diphenylphosphino)-2′-alkoxy-1,1′-binaphthyl

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Copyright information

© Springer-Verlag Berlin Heidelberg 2006

Authors and Affiliations

  • Cristiano Zonta
    • 1
  • Ottorino De Lucchi
    • 1
  • Raffaella Volpicelli
    • 2
  • Livius Cotarca
    • 2
  1. 1.Dipartimento di ChimicaUniversità Ca' Foscari di VeneziaVeneziaItaly
  2. 2.Zambon Group SpaLonigoItaly

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