HOF·CH3CN, a very efficient oxygen-transfer agent, was reacted with various aliphatic and aromatic vicinal diamino compounds. The products were the rare, vicinal dinitro derivatives formed in excellent yields and short reaction times. This is in contrast to other oxygen-transfer agents which tend to break the central C−C bond of the diamino precursor. This reaction was also used for making dinitro compounds with all four oxygens, being the [18]O isotope.

No abstract

No abstract

Tetrasubstituted epoxides, and especially electron‐depleted ones, generally are difficult to prepare. HOF·CH3CN complex, probably the best oxygen transfer agent known today, epoxidizes tetrasubstituted alkenes at 0 °C in a matter of minutes or less in excellent yields. HOF·CH3CN complex is very easy to prepare by bubbling diluted fluorine (commercial) through aqueous acetonitrile. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Epoxidation Epoxidation O 0218The First, General, Highly Efficient Method for Preparing Tetrasubstituted Epoxides Using HOF·CH 3 CN. -Readily available HOF·MeCN complex is proven to be the reagent of choice for epoxidation of electron-deficient tetrasubstituted alkenes. Exceptions are the heterocyclic compounds (XV) and (XVI) which can be reacted after ring-opening. The low yield of epoxydecalin (XIV) is attributed to partial decomposition during isolation. -(ROZEN*, S.; GOLAN, E.; Eur.