Lithium Ritter reaction

Mecamylamine Mecamylamine, M2,3,3-tetramethylnorboman-2-ylamine (14.2. 2), is synthesized from 2,3,3-trimethylnorbomen-2, which is reacted in a Ritter reaction conditions with hydrogen cyanide in concentrated snlfuric acid, giving 2,3,3-trimethylnorbor-nan-2-ylformylamine (14.2.1), the reduction of which by lithium aluminum hydride leads to mecamylamine (14.2.2) [32,33]. 

Alkyl iodides are cleaved in acetonitrile/lithium perchlorate to iodine and al-kyl.cations. These react prior to or after rearrangement in a Ritter reaction with acetonitrile to form N-alkylacetamides in 21% to 75%yield (Eq. (217) ) 4S8). 

If the reactions are carried out in a nitrile as solvent, rather than dichloromethane, using triflic acid as catalyst, a modified Ritter reaction takes place, and the intermediate nitrilium ion traps the liberated amine, forming an amidine (Scheme 67). In an earlier reaction cf. Scheme 67) the lithium perchlorate catalyzed reaction of sulfenyl chlorides with alkenes in the presence of nitriles had also given l-amido-2-sulfenyl adducts. Ritter products are also obtained in good yields by anodic oxidation (Pt or C, 1.2-1.4 V) of disulfides in acetonitrile, in the presence of excess alkene, using B114NBF4 as supporting electrolyte (Scheme 68). ... 

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