Alkanes Ritter reaction

This procedure constitutes the first example of one-step conversion of a /-alkane to the corresponding /-alkyfamine. Other hydrocarbons in this class, such as isobutane, have also been aminated with good results.7 Only a very limited number of convenient routes, e.g., the Ritter reaction, are available for the preparation of /-carbinamines. The present preparation illustrates a simple method that utilizes a novel substrate. 

Controlled potential electrolysis (cpe) of alkanes in acetonitrile/0.1 M TBABF4 yields acetamidoalkanes (Table 3). Voltammetry and coulometry indicate a 2e-oxidation to a carbenium ion that subsequently reacts with the nitrogen atom of acetonitrile in a Ritter reaction (Eq. 6) [20]. 

Exercise 15-24 It is possible to prepare amides from tertiary alcohols and alkane-nitriles, RCN, in concentrated sulfuric acid as the catalyst (Ritter reaction), as illustrated in the equation for the synthesis of W-fe/f-butylethanamide ... 

The acidic salts of heteropolyacids, in which the protons are partially substituted with Cs+, are active for acid-catalyzed reactions such as Friedel Crafts reactions, Ritter-type reactions, and skeletal isomerization of alkanes. The... 

In principle, any functionality capable of producing a carbenium ion under strongly acidic conditions will be able to participate in a Ritter-type reaction. Such classes of compounds include alcohols, aldehydes, alkanes, alkenes, alkyl halides, carboxylic acids, dienes, epoxides, esters, ethers, glycols, ketones, IV-methylolamides and oximes. Consequently, an enormous number of examples is reported and only a representative selection can be presented here. A comprehensive listing of examples reported up to 1966 is provided in the review by Krimen and Cota. ... 

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