Diallyl amines

Diallyl amine (7V-2-propenyl-2-propen-l-amine) [124-02-7] M 97.2, b 107-lll /760mm, 112 /760mm, dj 0.789, Dp 1.440, pK 9.42. Keep over KOH pellets overnight, decant and distil from a few pellets of KOH at atm pressure (b 108-111 ), then fractionate through a Vigreux column. [Vliet J Am Chem Soc 46 1307 7924 Org Synth Coll Vol I 201 1941.] The hydrochloride has m 164-165 (from Me2CO + EtOH). [Butler and Angels J Am Chem Soc 79 3128 1957.]... 

Starting from the appropriate diallyl amines or ethers, 4,5-dihydropyrroles and 4,5-dihydrofurans could be obtained in good yields in a matter of minutes. 

Morpholine also gives the allyhc amine in high yield. The reaction is thought to involve a known hydridopaUadium-catalyzed isomerization of alkynes to aUenes followed by reaction of the latter with the hydridopalladium complex to give 1-phenyl-substituted q -allylpalladium complexes. These complexes react with amines affording the allylic amines. Primary amines give the diallylic amines. An intramolecular version has been developed for the synthesis of 2-(2-phenyl)-pyrroUdines and -piperidines [319]. 

Diallyl amine has been prepared from allyl amine and allyl bromide,1 and from allyl amine and allyl chloride.2 Experiments on these methods showed that the resulting product contained relatively large amounts of triallyl amine and mono-allyl amine and it was very difficult to isolate pure diallyl amine. The above synthesis from diallyl cyanamide, which has recently appeared in the literature,3 is more satisfactory than the older methods. 

A group transfer tandem addition of bromotrichloromethane to diallyl amine 157 has been reported [95SC3529]. The radical reaction can be initiated using either azobisisobutyronitrile (AIBN) or manganese(III) acetate electrochemically. It should be noted that the cis diastereomer is formed as the major product. 

Hall [4] prepared crossliked polymers that were effective as adhesives by UV curing of the neutralization product of diallylamine with selected carboxylic acids, (IV). Additional UV curable diallyl amine adhesives, (V), were prepared by Milne [5]. 

Dimethyl-2-oxo-butyliden)-(2-methyl-propanoyl)- E14b, 236 [C(C1) —NH-Acyl - C = N-Acyl] 3-Aza-bicyclo 3.2.0]heptan l(or 2)-Methyl-3-propanoyl-E17e, 160 (Diallyl-amin/hv) 6-Aza-bicyclo 3.1.0 hexan 2-(2-Tetrahydropyranyloxy)-(e.xo/ endo) E16c, 404 (En + R —OH)... 

A,A-Disubstituted amides can be converted to alkynyl ketones by treatment with alkynylboranes RCONR2 + (R C=C)3B RCOC=CR. Lactams react with triallylborane to give cyclic 2,2-diallyl amines after treatment with methanol, and then aqueous hydroxide. Triallylborane reacts with the carbonyl group of lactams, and after treatment with methanol and then aqueous NaOH gives the... 

Diallyl amine (A -2-propenyl-2-propen-l-amine) [124-02-7] M 97.2, b 107-lll /760mm, 112 /760mm, dj 0.789, 1.440, pK 9.42. Keep over KOH pellets overnight, decant and distil... 

As 4-atom fragments, allylamines are often used for the synthesis of 1,2-azaborolidines, 1,2-azoniaboratolidines, 1,2-azaboroles, and 1,2-azoniaboratoles. 1,2-Azaborolidines are generally formed if borane-amine adducts are thermally burdened in the presence of alkyl-, allyl-, and diallyl amines. These reactions can also be described as hydroborations of diallyl compounds (Equations (22) and (23)) <70ZOB1528,76IOC2803>. 

Lewis acid-catalyzed ene cyclization reactions at low temperature have been shown to yield substituted piperidines with a high diastereomeric ratio <05TL6611>. Organolanthanide-catalyzed cyclization-silylation has been developed as a powerful strategy for the piperidine rings found in alkaloids. As a prototypical example, the simple diallyl amine 174 was cyclized to 175 in the presence of 5 mol % of the catalyst shown in Scheme 50 and a suitable silane terminator <0512631>. 

Ethyl-3-diallylaminopropionate (XIV) was synthesized from ethyl 3-bromopropionate (20 g, 0.111 mol) to which diallyl-amine (29 g, 0.3 mol) was added slowly with stirring and heating at 100-105°C. After complete addition, heating was continued for another 15 min. The mixture then was cooled and water was added. The solution was basified with ammonia and the product extracted with chloroform and purified by distillation. 

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