Gabriel synthesis

Gabriel synthesis
Named after Siegmund Gabriel
Reaction type Substitution reaction
Identifiers
Organic Chemistry Portal gabriel-synthesis
RSC ontology ID RXNO:0000103

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−.

  1. ^ 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.
  2. ^ 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.
  3. ^ Mitsunobu, O. Compr. Org. Synth. 1991, 6, 79–85. (Review)
  4. ^ S. Gabriel (1887). "Ueber eine Darstellung primärer Amine aus den entsprechenden Halogenverbindungen". Chemische Berichte. 20: 2224. doi:10.1002/cber.18870200227.
  5. ^ 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.
  6. ^ Hendrickson, J (1975). "New "Gabriel" syntheses of amines". Tetrahedron. 31 (20): 2517–2521. doi:10.1016/0040-4020(75)80263-8.
  7. ^ Ulf Ragnarsson; Leif Grehn (1991). "Novel Gabriel Reagents". Acc. Chem. Res. 24 (10): 285–289. doi:10.1021/ar00010a001.