Alkyl Nitrites as Valuable Reagents in Organic Synthesis

Alkyl nitrites are inexpensive, mild, relatively stable and easy-to-handle alkyl esters of nitrous acid, that can be prepared simply and used in various synthetic reactions. Alkyl nitrites were discovered in the 19th century and were initially used as medical vasodilators. After several years it was observed, that alkyl nitrites are useful chemical reagents, especially as efficient NO source, consequently these were used for diazotization and as nitrating agent or oxidant. In this review several important and novel applications of alkyl nitrites in organic transformations are reported. Keywords: Alkyl nitrites, alternative Sandmeyer reaction, arylation, nitration, oxidation, oximes.