Gabriel synthesis


An important laboratory use involves the Gabriel synthesis of a-amino-acids.  [c.312]

Benzylamine may be obtained by the Gabriel synthesis, which depends upon the use of potassium phthalimide. The latter upon heating with benzyl  [c.559]

Chapter IV. a-Chloromethylnaphthalene (IV,23) benzylamine (Gabriel synthesis) (IV,39) i r.N -dialkylanilines (from amines and trialkyl orthophosphates) (IV,42) a-naphthaldehyde (Sommelet reaction) (IV,120) a-phenyl-cinnamic acid (Perkin reaction using triethylamine) (IV,124) p-nitrostyrene (IV,129) p-bromonaphthalene and p naphthoic acid (from 2 naphthylamine-1 -sulphonic acid) (IV,62 and IV,164) diphenic acid (from phenanthrene) (IV,165).  [c.1191]

The Gabriel Synthesis of Primary Alkylamines  [c.929]

THE GABRIEL SYNTHESIS OF PRIMARY ALKYLAMINES  [c.929]

A method that achieves the same end result as that desired by alkylation of ammonia but which avoids the formation of secondary and tertiary amines as byproducts is the Gabriel synthesis Alkyl halides are converted to primary alkylamines without contam mation by secondary or tertiary amines The key reagent is the potassium salt of phthal imide prepared by the reaction  [c.929]

In Its overall design this procedure is similar to the Gabriel synthesis a nitrogen nude ophile IS used m a carbon-nitrogen bond forming operation and then converted to an ammo group m a subsequent transformation  [c.931]

Gabriel synthesis (Section 22 8) Method for the synthesis of primary alkylamines in which a key step is the formation of a carbon-nitrogen bond by alkylation of the potassium salt of phthalimide  [c.1284]

The Gabriel Synthesis of Primary Alkylamines  [c.929]

THE GABRIEL SYNTHESIS OF PRIMARY ALKYLAMINES  [c.929]

Gabriel synthesis (Section 22.8) Method for the synthesis of primary alkylamines in which a key step is the formation of a carbon-nitrogen bond by alkylation of the potassium salt of phthalimide.  [c.1284]

Robinson-Gabriel Synthesis 249  [c.219]

Robinson-Gabriel Synthesis  [c.249]

The modified procedure involves refluxing the N-substituted phthaUmide in alcohol with an equivalent quantity of hydrazine hydrate, followed by removal of the alcohol and heating the residue with hydrochloric acid on a steam bath the phthalyl hydtazide produced is filtered off, leaving the amine hydrochloride in solution. The Gabriel synthesis has been employed in the preparation of a wide variety of amino compounds, including aliphatic amines and amino acids it provides an unequivocal synthesis of a pure primary amine.  [c.560]

Gabriel synthesis Gattermaim aldehyde reaction Gattermann reaction Gattermann-Kocll reaction Gomberg-Hey reaction Grignard reaction  [c.1210]

The Gabriel synthesis is based on work carried out by Siegmund Gabriel at the Uni versity of Berlin in the 1880s A detailed discussion of each step in the Gabriel synthesis of benzylamine can be found in the October 1975 Journal of Chemical Education (pp 670-671)  [c.929]

Aryl halides cannot be converted to arylammes by the Gabriel synthesis because they do not undergo nucleophilic substitution with N potassiophthalimide m the first step of the procedure  [c.930]

Among compounds other than simple alkyl halides a halo ketones and a halo esters have been employed as substrates m the Gabriel synthesis Alkyl p toluenesul fonate esters have also been used Because phthalimide can undergo only a single alkyl ation the formation of secondary and tertiary amines does not occur and the Gabriel synthesis is a valuable procedure for the laboratory preparation of primary amines  [c.930]

Alkylation of phthalimide The Gabriel synthesis (Section 22 8) The potassium salt of phthalimide reacts with alkyl hal ides to give N alkylphthalimide deriva fives Hydrolysis or hydrazinolysis of this derivative yields a primary alkylamine  [c.956]

Isobutylamine and 2 phenylethylamine can be prepared by the Gabriel synthesis ten butyl amine N methylbenzylamine and aniline cannot  [c.1245]

Gabriel synthesis, 7, 33 aziridines, 7, 81-82 thiazoles, 6, 302 Galanthamine structure, 4, 548 Galbacin NMR, 4, 574 Gelatin hardeners for  [c.640]

Ring transformations heterocyclic compounds reviews, 1, 70 Ring-chain tautomerism polyheteroatom six-membered rings, 3, 1056 Ripariochromene A synthesis, 3, 751, 755 Robinson-Gabriel synthesis oxazoles, 6, 216  [c.837]

Two common rnethods of aziridine synthesis, namely the Wenker method (through -amino alcohols) and the Neber rearrangement (through oxime tosylates) are inapplicable to the synthesis of fused steroidal aziridines. Only the Gabriel synthesis, i.e., ring closure of -halo amines, has been successfully adapted to the steroid system. The recent discovery of additions to olefins of pseudohalogen reagents such as iodine isocyanate, iodine azide, chlorine azide and bromine azide has provided a source of -halo amines which are otherwise difficult to obtain. Trans-halo amines undergo ring closure to aziridines, whereas the cw-isomers eliminate HX on treatment with base to give ketones or other products. A useful complement to pseudohalogen adducts is provided by j8-mesyIoxy azides, obtained by azide ion opening of epoxides followed by mesylation. Another general method of aziridine synthesis, namely nitrene addition to double bonds, has seen only limited application to date due to lack of selectivity of the nitrene reagent, which gives C—H insertion products as well as addition products.  [c.22]

An alternative to Gabriel synthesis is based on the alkylation of tnfluoro-acetamide [770, 777[ or Al-benzyl triflamide [772] in place of the classical phtalimide (equations 96 and 97).  [c.471]

The Gabriel synthesis is based on work carried out by Siegmund Gabriel at the University of Berlin in the 1880s. A detailed discussion of each step in the Gabriel synthesis of benzylamine can be found in the October 1975 Journal of Chemical Education (pp. 670-671).  [c.929]

Aryl halides cannot be converted to arylanines by the Gabriel synthesis because they do not undergo nucleophilic substitution with A-potassiophthalimide in the first step of the procedure.  [c.930]

Among compounds other than simple alkyl halides, a-halo ketones and a-halo esters have been employed as substrates in the Gabriel synthesis. Alkyl p-toluenesul-fonate esters have also been used. Because phthalimide can undergo only a single alkylation, the formation of secondary and tertiary anines does not occur, and the Gabriel synthesis is a valuable procedure for the laboratory preparation of primary amines.  [c.930]

In its overall design, this procedure is similar- to the Gabriel synthesis a nitrogen nucleophile is used in a carbon-nitrogen bond-fonning operation and then converted to an fflnino group in a subsequent transfor-mation.  [c.931]

Alkylation of phthalimide. The Gabriel synthesis (Section 22.8) The potassium salt of phthalimide reacts with alkyl halides to give A/-alkylphthalimide derivatives. Hydrolysis or hydrazinolysis of this derivative yields a primary alkylamine.  [c.956]

Isobutylamine and 2-phenylethylamine can be prepared by the Gabriel synthesis tert-butyl-amine, A-methylbenzylamine, and aniline cannot.  [c.1245]

Onaka demonstrated the utility of a modified Fisher method in the one-step synthesis of oxazole alkaloid Halfordinol (16) in higher overall yield than previously reported by Robinson-Gabriel synthesis.  [c.236]


See pages that mention the term Gabriel synthesis : [c.569]    [c.121]    [c.930]    [c.11]    [c.113]    [c.33]    [c.81]    [c.81]    [c.929]    [c.930]   
See chapters in:

Named organic reactions 2nd edition  -> Gabriel synthesis


Textbook on organic chemistry (1974) -- [ c.559 , c.560 , c.569 ]

Carey organic chemistry (0) -- [ c.929 , c.930 , c.956 ]

Organic chemistry (0) -- [ c.929 , c.930 , c.956 ]

Named organic reactions 2nd edition (2005) -- [ c.83 , c.130 , c.131 ]