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N-oxides, also referred to as amine oxides, are organic compounds that contain the functional group N+-O-. Amine oxides are weak bases and highly polar molecules. Small amine oxides are found to be hydrophilic in nature and hence possess excellent water solubility.
In organic synthesis, some of the organic reactions involve the N-oxide. The Cope reaction is an elimination reaction of the N-oxide of a tertiary amine to form an alkene. Similarly, the Meisenheimer rearrangement involves certain N-oxides which rearrange to hydroxylamines in a 1,2-rearrangement or 2,3-rearrangment. The Polonovski reaction involves a tertiary N-oxide substrate which is cleaved by acetic acid anhydride to the corresponding acetamide and aldehyde. Pyridine N-oxide is often used as an oxidizing agent in organic synthesis.
Amine oxides have other wide ranging applications, for example in the formulation of topical pharmaceuticals. Furthermore, these compounds serve as stabilizers, thickeners, emollients, and emulsifiers. Amine oxide is an amphoteric surfactant widely used in conjunction with other surfactants. As surfactants, they are used in shampoos, conditioners, detergents, and hard surface cleaners.