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DEMJANOV REARRANGEMENT

Demjanov rearrangement is the chemical reaction of primary amines with nitrous acid to give rearranged alcohols. It involves substitution by a hydroxyl group with a possible ring contraction and opening of ring. The Tiffeneau–Demjanov ring expansion, Tiffeneau–Demjanov rearrangement, or TDR, provides an easy way to increase beta amino-substituted cycloalkanols in size by one carbon. Ring sizes from cyclopropane to cyclooctane are able to undergo Tiffeneau–Demjanov ring expansion with some degree of success. Yields decrease as initial ring size increases, and the ideal use of TDR is for synthesis of five, six, and seven membered rings.