Hydrocarbons aliphatic, acetamidation

The commercial polymers are generally resistant to aqueous acids and alkalis although they are attacked by concentrated sulphuric acid. As might be expected of a highly polar polymer it is not dissolved by aliphatic hydrocarbons but solvents include dimethyl formamide and dimethyl acetamide. 

It was also found recently that direct selective substitution of aliphatic hydrocarbons via a supposedly electrophilic mechanism can be achieved by use of F-TEDA-BF4 [202]. Depending on the exact reaction conditions, either alkyl fluorides or Ritter-type products are obtained (Scheme 2.91). Relatively short reaction times favor the formation of the fluorides, longer heating with F-TEDA-BF4 in acetonitrile favors the formation of acetamides, especially in the presence of additional BF3 OEt2 as Lewis acid catalyst [203]. 

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