Dinitrogen trioxide reactions with alkenes

The earliest reported Fxs were the result of the reaction of nitrous acid with naturally occurring alkenes being the identified intermediate a a-nitrooxime that suffers dehydration with cyclization. Apart from these conditions, the most recent Fxs synthesis descriptions have involved reactions between alkenes and dinitrogen trioxide (Fig. 3), nitroalkanes and aluminum trichlo-... 

The reaction of alkenes with nitric oxide (NO), a mixture of nitric oxide and oxygen, or dinitrogen trioxide leads to /i-nitroso nitro compounds ( / -nitrosites or pseudo-nitrosites), which can convert to nitroso dimers79. Nitroalkenes are common byproducts in these reactions. The formation of /i-nitroso nitro compounds in the reaction between alkenes and nitric oxide is explained by the presence of nitrogen dioxide and dinitrogen trioxide in the nitric oxide. The reaction may be initiated by the attack of the N02 radical on the alkene to give a /i-nitroalkyl radical which then couples with nitric oxide. 

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