acylation
process of adding an acyl group to a compound
amide
organic compound that contains a carbonyl () linked to a nitrogen atom through a bond. It has a general stoichiometry.
amination
process of adding an amine group to a compound
amine
organic compound that is a derivative of ammonia (NH3), in which one or more hydrogen atoms are replaced by alkyl or aryl units (R), forming single bonds
aryl diazonium salt
one of a group of salts of the general formula ArN2X, where Ar is an aryl group and X is an anion, such as benzenediazonium chloride (C6H5N(N)Cl)
azide
compound containing the group N3 combined with an element or a radical
azo compound
organic compound bearing the functional group diazenyl , in which R and R′ can be either aryl or alkyl
azo coupling
electrophilic aromatic substitution reaction between an aryl diazonium salt and another aromatic compound that produces an azo compound
Curtius rearrangement
reaction that involves the thermal decomposition of acyl azides to produce an isocyanate intermediate, which is then hydrated and decarboxylated to form a primary amine
diazotization
process of converting a primary amine into its diazonium salt
Gabriel synthesis
reaction in which alkyl halides are treated with phthalimide and a strong base, followed by the addition of hydrazine, yielding a primary amine
heterocycle
organic compound containing a ring of atoms of at least two elements (one of which is generally carbon)
Hofmann elimination reaction
process in which the primary amine is treated with excess methyl iodide (CH3I) and then the resultant ammonium salt is distilled under pressure with silver oxide (Ag2O), yielding the least substituted alkene
Hofmann rearrangement
reaction in which primary amides are treated with a halogen and a base and rearranged into an isocyanate intermediate that then converts into a primary amine following the loss of carbon dioxide in the presence of water
imine
organic compound containing the group or its substituted form, NR, that is derived from ammonia by replacement of two hydrogen atoms by a hydrocarbon group or other nonacid organic group
isocyanate
highly reactive, low-molecular-weight organic compound with the formula
nitrile
organic compound that has a carbon triple bonded to a nitrogen with RCN stoichiometry
oxime
organic compound containing the divalent group and obtained mainly by the action of hydroxylamine on aldehydes and ketones
polyalkylation
reaction that occurs when multiple alkyl groups are added instead of just the desired one alkyl group
reductive amination
two-step form of amination that involves the conversion of a carbonyl group to an amine through an imine () or an oxime () intermediate
Sandmeyer reaction
replacement reaction that occurs via copper reagents (e.g., CuCl, CuBr, CuCN)