RCOOOR

RCOOOR is a shorthand notation used in organic chemistry to denote a perester, a class of organic compounds containing a peroxide linkage between an acyl fragment and an alkoxy fragment. Its general structure is R-CO-O-O-R', where R is an acyl substituent and R' is an alkyl or aryl group. Peresters are a subset of organic peroxides and are distinguished by the presence of the O-O bond adjacent to an ester moiety. The term RCOOOR appears in reaction schemes and nomenclature to indicate this functional motif.

Synthesis and properties: Peresters are typically prepared from carboxylic acid derivatives and hydroperoxides or related reagents under appropriate conditions. They are generally less stable than simple esters because the O-O bond is relatively weak and can homolyze under thermal or mechanical stress. As a result, peresters can decompose exothermically to generate radicals, a feature that underpins their use as radical initiators but also contributes to safety hazards. They are often liquids or low-melting solids and require storage away from heat, light, and shocks.

Applications: The primary use of peresters is as radical initiators in polymerization and in various organic-synthesis applications where controlled radical generation is desired. They can initiate polymerization of acrylates, styrenes, and other vinyl monomers and are also employed in oxidation protocols and other transformations that benefit from a clean radical source.

Safety and regulation: Peresters are typically classified as organic peroxides and are subject to strict handling and storage regulations because of their potential for explosive decomposition. Proper containment, temperature control, and regulatory compliance are essential in any handling or procurement.

See also: Organic peroxide, ester, radical initiator, hydroperoxide.