5.2.4 Synthesis of Nitrile

The readily accessible oximes from aldehydes and hydroxyl amine readily undergo dehydration in the presence of DCC to nitriles in quantitative yields (Scheme 6).

Scheme 7

5.2.5 Synthesis of a,b -Unsaturated Esters

The dehydration of β -hydroxy esters can be efficiently carried out using DCC to give α,β -unsaturated ester (Scheme 7).

Scheme 8

5.2.6 Heterocyclization Reactions

DCC is used as reactant as well as reagent in heterocyclization reactions. For an example, barbituric acid and its derivatives can be prepared by the reaction of malonic acid with DCC (Scheme 8).

Scheme 9

5.2.7 Heterocyclization Reactions

A mixture of DCC and DMSO catalyzes the oxidation of alcohols to aldehydes or ketones in the presence of acid catalyst. The reaction is called Pfitzner-Moffatt oxidation. A sulfur ylide is formed with base abstracts the α -proton, generating dimethyl sulfide and the aldehyde or ketone (Scheme 9).

 

Scheme 10