Demjanov Rearrangement

Demjanov Rearrangement

Demjanov Rearrangement: One of the most familiar methods for the generation of carbonium ions is the determination of primary amines by means of nitrous acid. In many cases the initially formed carbonium ion undergo rearrangement to yield the rearranged products. Thus n-propylamine on treatment with nitrous acid yields some n-propyl alcohol together with a major proportion of isopropyl alcohol. This reaction forms the basis of Demjanov's method of expanding and contracting alicyclic ring systems (Demjanov Rearrangement). 
Demjanov Rearrangement

when cyclobutylmethyl amine is treated with nitrous acid it gives both cyclobutylcarbinol (2) and cylcopentanol (4) besides methylenecyclobutene  (1) and cyclopentene (3).
Demjanov Rearrangement
Demjanov Rearrangement

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