The Gabriel reagent is widely used as a nucleophilic aminating agent since its reactivity is reliable and its handling is easy. Recently, a variety of aminating agents analogous to the Gabriel reagent have been reported, for example, tert-butyl methyl iminodicarboxylate, N-(tert-butoxycarbonyl)-p-toluenesulfonamide, sodium diformamide, and di-tert-butyl iminodicarboxylate.

The potassium salt of imide 1 reacts with alkyl halide to give imide 2. 2 is treated with base or acid to give either N-Boc-amine 3 or N-metoxycarbonylamine 4, respectively. Moreover, 1 also serves as an acid nucleopile in the Mitsunobu reaction to allow for the conversion of hydroxyl groups to amino groups. Therefore, 1 is a useful reagent to give mono protected amines.
On the other hand, acetoxime O-(2,4,6-trimethylphenyl)sulfonate 5 has been reported as a useful electrophilic aminating agent. 5 reacts with Grignard reagent in the presence of a catalytic amount of magnesium chloride to afford primary amines in good yields.

A1137	A1441	I0497
B1734	D2361	D1672
M1182	H0093	H0258
H0196	H0530	D1899
B2303	B1648	A1632
C1757	M0343	M0886
P1235	P0403	D2479
I0510	B2857	T1184

A1137	4-Amino-1,2,4-triazole
A1441	Acetoxime O-(2,4,6-Trimethylphenylsulfonate)
I0497	Di-tert-butyl Iminodicarboxylate
B1734	Diethyl N-(tert-Butoxycarbonyl)phosphoramidate
D2361	Diethyl Phosphoramidate
D1672	Diphenylphosphoryl Azide
M1182	Ethyl O-Mesitylsulfonylacetohydroxamate [Precursor of the Powerful Aminating Reagent]
H0093	Hexamethylenetetramine
H0258	Hydroxylamine Hydrochloride
H0196	Hydroxylamine Sulfate
H0530	Hydroxylamine-O-sulfonic Acid
D1899	N,O-Dimethylhydroxylamine Hydrochloride
B2303	N-(tert-Butoxycarbonyl)-2-nitrobenzenesulfonamide
B1648	N-(tert-Butoxycarbonyl)-p-toluenesulfonamide
A1632	N-Allyloxycarbonyl-2-nitrobenzenesulfonamide
C1757	N-Carbobenzoxy-2-nitrobenzenesulfonamide
M0343	O-Methylhydroxylamine Hydrochloride
M0886	O-Methylhydroxylamine Hydrochloride (ca. 40% in Water, ca. 5.4mol/L)
P1235	Phthalimide DBU Salt
P0403	Phthalimide Potassium Salt
D2479	Sodium Diformylamide
I0510	tert-Butyl Methyl Iminodicarboxylate
B2857	tert-Butyl [Bis(4-methoxyphenyl)phosphinyloxy]carbamate
T1184	Trimethylsilylmethyl Azide