iminoxime

Iminoxime is a chemical compound with the general formula R1R2C=NOH, where R1 and R2 are organic substituents. It is characterized by the presence of an imine group (C=N) directly attached to a hydroxyl group (OH). Iminoximes are also known as oxime ethers or oxime esters depending on the specific structure, although the term iminoxime specifically refers to the imine functional group.

These compounds are typically formed through the reaction of an aldehyde or ketone with hydroxylamine. The reaction involves the nucleophilic addition of hydroxylamine to the carbonyl carbon, followed by the elimination of a water molecule. The resulting iminoxime can exist as various stereoisomers, specifically syn and anti isomers, due to restricted rotation around the carbon-nitrogen double bond.

Iminoximes find applications in organic synthesis as intermediates and protecting groups. They can be further reacted to form other functional groups, or the oxime moiety can be used to temporarily mask a carbonyl group during multi-step syntheses. The stability and reactivity of iminoximes can be influenced by the nature of the R1 and R2 substituents. They are generally considered moderately stable compounds.