Nitryl iodide synthesis

The synthetic applications of this reagent to the synthesis of nitroalkenes have been known since the 1960s.60 Nitration of alkenes with nitryl iodide, generated in situ from iodine and silver nitrite, is convenient for the synthesis of P-nitrostyrenes with various functional groups.61 This method is applied to the synthesis of ortho-methoxylated phenylisopropylamines, which are potent serotonine agonists (Eq. 2.31).62... 

Nitration of acetylenes with nitryl iodide followed by elimination of HI gives nitroacetylenes, but nitroacetylenes are too thermally unstable to be useful for organic synthesis.77 Recently, nitro-trimethylsilyl-acetylenes are prepared as stable nitroacetylenes by the reaction of bis(trimethylsily)acetylene with nitronium tetrafluoroborate (Eq. 2.39).78... 

Nitryl iodide, from iodine with silver nitrite or from NO2 and iodine, adds to alkenes, generally in ether at room temperature, by a radical mechanism. Yields are 50-90%. The products yield nitroalkenes on treatment with base, a sequence used recently in the preparation of intermediates (ArCH—CMeNOa) for amphetamine analogs. The reaction is also a key step in the a-methylenebuty-rolactone synthesis shown in Scheme... 

Nitryl iodide has been shown to add to substituted styrenes, an observation which has thus facilitated synthesis of substituted B-... 

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