PUMMERER AND RELATED REARRANGEMENTS IN 2-ACYL-1,3-DITHIANE 1-OXIDES

Authors
PAGE PCB SHUTTLEWORTH SJ MCKENZIE MJ SCHILLING MB TAPOLCZAY DJ
Citation
Pcb. Page et al., PUMMERER AND RELATED REARRANGEMENTS IN 2-ACYL-1,3-DITHIANE 1-OXIDES, Synthesis, (1), 1995, pp. 73-77
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
1
Year of publication
1995
Pages
73 - 77
Database
ISI
SICI code
0039-7881(1995):1<73:PARRI2>2.0.ZU;2-4
Abstract
syn- and anti-2-Acyl-2-alkyl-1,3-dithiane 1-oxides, when treated with trifluoroacetic anhydride, undergo either an unexpected Pummerer rearr angement or equilibration in near quantitative yield, depending upon t he reaction conditions; 2-acyl-1,3-dithiane 1-oxides readily undergo a related rearrangement upon treatment with Lewis acid or exposure to s ilica gel.