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Contribution to the Transformations of 1‐Thioflavonoids with Hypervalent Oxidants
Author(s) -
Somogyi László
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940920
Subject(s) - chemistry , dehydrogenation , periodate , hypervalent molecule , ceric ammonium nitrate , permanganate , oxide , inorganic chemistry , ammonium , sulfoxide , ammonium nitrate , redox , organic chemistry , reagent , catalysis , polymer , grafting
Permanganate oxidation transforms 1‐thioflavanone ( 1a ) to the corresponding 1,1‐dioxide 1c . Periodate oxidation of 1a affords in the cold mainly the corresponding sulfoxide 1b , and that of 1a or 1‐thioflavone 1‐oxide ( 2b ) provides on heating 1‐thioflavone 1,1‐dioxide ( 2c ). Since 1b is resistant to ceric ammonium nitrate (CAN) the mechanism of the dehydrogenation reaction of 1a with CAN furnishing 1‐thioflavone ( 2a ) with transient formation of 1b , as suggested in the literature, is questionable.