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Synthesis 1995; 1995(1): 73-77
DOI: 10.1055/s-1995-3857
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Pummerer and Related Rearrangements in 2-Acyl-1,3-Dithiane 1-Oxides

Philip C. Bulman Page* , Stephen J. Shuttleworth, Michael J. McKenzie, Mark B. Schilling, David J. Tapolczay
  • *Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Oxford Street, Liverpool L69 3BX, England
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Publication Date:
31 December 2000 (online)

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syn- and anti-2-Acyl-2-alkyl-1,3-dithiane 1-oxides, when treated with trifluoroacetic anhydride, undergo either an unexpected Pummerer rearrangement or equilibration in near quantitative yield, depending upon the reaction conditions; 2-acyl-1,3-dithiane 1-oxides readily undergo a related rearrangement upon treatment with Lewis acid or exposure to silica gel.

Pummerer - dithiane - DiTOX - rearrangement - thioacetal