Telomerization of Butadiene with Nitroalkanes

Methylene compounds which contain only one electronegative group are normally inactive in telomerization. One exception is the nitroalkanes, which react very smoothly with butadiene [21, 22]. The telomerization of nitromethane in the presence of [PdCl2(PPh3)2] and sodium hydroxide at room temperature produces three nitro-compounds which are accompanied by a small amount of branched products (Equation 18). 

The telomer with two octadienyl chains fixed on the nitromethane, the 9-nitro-1,6,11,16-heptadecatetraene, can be used to synthesize civetonedi-carboxylic acid, a precursor of cis-civetone (Equation 19) [23]. 

Besides nitromethane, nitroethane, 1- and 2-nitropropane and nitrocyclo-hexane can also be telomerized. The nitroethane telomer was used for the synthesis of recifeiolide, a naturally occuring 12-membered lactone (Equation 20) [24]. 

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Nitrodienes by Telomerization of Butadiene with Nitroalkanes General Procedure12 ... 

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