The Gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Traditionally, the reaction uses potassium phthalimide.[1][2][3] The reaction is named after the German chemist Siegmund Gabriel.[4]
The Gabriel reaction has been generalized to include the alkylation of sulfonamides[5] and imides, followed by deprotection, to obtain amines (see Alternative Gabriel reagents).[6][7]
The alkylation of ammonia is often an unselective and inefficient route to amines. In the Gabriel method, phthalimide anion is employed as a surrogate of H2N−.
^Sheehan, J. C.; Bolhofer, V. A. (1950). "An Improved Procedure for the Condensation of Potassium Phthalimide with Organic Halides". J. Am. Chem. Soc.72 (6): 2786. doi:10.1021/ja01162a527.
^Gibson, M.S.; Bradshaw, R.W. (1968). "The Gabriel Synthesis of Primary Amines". Angew. Chem. Int. Ed. Engl.7 (12): 919. doi:10.1002/anie.196809191. S2CID 95888531.
^Mitsunobu, O. Compr. Org. Synth.1991, 6, 79–85. (Review)
^S. Gabriel (1887). "Ueber eine Darstellung primärer Amine aus den entsprechenden Halogenverbindungen". Chemische Berichte. 20: 2224. doi:10.1002/cber.18870200227.
^Carey, Francis A.; Sundberg, Richard J. (2007). Advanced Organic Chemistry: Part B: Reactions and Synthesis (5th ed.). New York: Springer. p. 230. ISBN 978-0387683546.
^Hendrickson, J (1975). "New "Gabriel" syntheses of amines". Tetrahedron. 31 (20): 2517–2521. doi:10.1016/0040-4020(75)80263-8.
The Gabrielsynthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Traditionally, the reaction uses potassium phthalimide...
which use high-mass reagents that ultimately become waste; and the Gabrielsynthesis, which produces a stoichiometric quantity of phthalic acid salts....
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of 1,4-aminodiketones to oxazoles by dehydration in the Robinson–Gabrielsynthesis In the case of aryl–alkyl ketones, with sulfur and an amine give amides...
was made in 1887, when he discovered the GabrielSynthesis with his partner James Dornbush. The GabrielSynthesis is a reaction which synthesizes pure primary...
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precipitates. This compound is a commercially available reagent used in the Gabrielsynthesis of amines. P. L. Salzberg and J. V. Supniewski (1941). "β-Bromoethylphthalimide"...
100 °C or with potassium hydroxide in absolute ethanol, is used in the Gabrielsynthesis of primary amines, such as glycine. Kladnoite is a natural mineral...
employed on an industrial scale. Selectivity is also assured in the Gabrielsynthesis, which involves organohalide reacting with potassium phthalimide....
Fischer oxazole synthesis or Robinson-Gabrielsynthesis, where the oxazole ring is constructed via either synthesis. The Fischer oxazole synthesis has also been...
reaction allows phthalimide anion to be used as amine precursor in the Gabrielsynthesis. Illustrative of the condensation of hydrazine with a simple carbonyl...
developed, such as the Delépine reaction, which uses hexamine. The Gabrielsynthesis, involving the use of an equivalent to NH2−, only applies to primary...
Amines may also be prepared from alkyl halides in amine alkylation, Gabrielsynthesis and Delepine reaction, by undergoing nucleophilic substitution with...
waveforms through methods including subtractive synthesis, additive synthesis and frequency modulation synthesis. These sounds may be altered by components...
erythrose with sodium phthalimide gives the acid 2; hydrazinolysis (cf Gabrielsynthesis) then leads to the amino acid 3. Displacement of chlorine in pyrimidine...
4-chloro-1-butyl ester. The chloride is then converted to an amino group via a Gabrielsynthesis (with potassium phthalimide) followed by hydrazinolysis (Ing–Manske...
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