alkoxycarbonyl

An alkoxycarbonyl is a functional group characterized by the fragment -COOR', where the carbonyl carbon is bonded to an alkoxy group (OR') and R' is typically an alkyl or aryl group. This group is the acyl portion of esters and related carbamate derivatives, and it is commonly referred to as the alkoxycarbonyl substituent in systematic naming. When R' is a specific alkyl group, names such as methoxycarbonyl (–COO–CH3) or ethoxycarbonyl (–COO–C2H5) are used to describe particular ester motifs.

In organic synthesis, alkoxycarbonyl groups are central to both esters and carbamates. Protecting groups based on this motif include the tert-butoxycarbonyl group (Boc) and the benzyloxycarbonyl group (Cbz or Z), which convert amines into carbamates to prevent undesired reactions during multi-step sequences. The Boc group, for example, features a tert-butyl alkoxy group attached via an oxygen to the carbonyl carbon, forming a tert-butyl carbonate derivative used to protect amines; it can be removed under acidic conditions to reveal the free amine. Other alkoxycarbonyl derivatives, such as methyl or ethyl esters, are common end products of esterification reactions.

Reactivity of alkoxycarbonyl groups includes hydrolysis (saponification) to yield carboxylic acids and alcohols, as well as transesterification and, in protecting-group contexts, deprotection to restore the original functionality. The term captures the widespread presence of the -COOR' motif across esters, carbonates, and related protective or activating groups in organic chemistry.