The complex of hypofluorous acid with acetonitrile � HOF�CH3CN is probably the best oxygen transfer agent organic chemistry has in its arsenal today. It is readily prepared by bubbling dilute fluorine through aqueous acetonitrile, does not need any isolation or purification and is stable for hours at 0 oC. We will demonstrate the synthesis of some �impossible� target molecules achieved by using it. Thus, since the origin of the active oxygen is in water, it has been used to easily and economically prepare alcohols with [18]O isotope. Recently, it was also used to construct novel and long sought after conjugated oligothiophenes containing the unique arrangement of internal adjacent [all]-S,S-oxygenated thiophene fragments with a the lowest HOMO-LUMO gap so far. Selenones, is a family of compounds which does not have a general method for its preparation. In fact, there are numerous selenones which could not be made, each for its own reasons. HOF�CH3CN is able to transfer two oxygen atoms to the Se atom under very mild conditions and almost instantaneously  .

Unique oxygen transfer reactions with HOF�CH<sub>3</sub>CN

247th National Meeting (2014)

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Unique oxygen transfer reactions with HOF�CH3CN

Unique oxygen transfer reactions with HOF�CH₃CN