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Zeitschriftenartikel:

U. Jordis, F. Grohmann, B. Küenburg:
"Optimized synthesis of some γ,γ-disubstituted allylamines";
Organic Preparations and Procedures International, 29 (1997), 5; S. 549 - 560.



Kurzfassung englisch:
One of the title amines, 3-methyl-2-buten-1-amine (I) was prepd. by the rearrangement of trichloroacetimidates of a,a-disubstituted allyl alcs. Thus, 2-methyl-3-buten-2-ol in THF contg. g,g-disubstituted allyl NaH was treated with trichloroacetonitrile to give .apprx.98% 2,2,2-trichloroethanimidic acid 1,1-dimethyl-2-propenyl ester which was rearranged in refluxing toluene to 71% N-(3-methyl-2-butenyl)-2,2,2-trichloroacetamide. This compd. was hydrolyzed to 80% I in aq. DMF with KOH. Other title amines, of high nucleophilicity, were prepd. by redn. of acrylonitriles by AlH3, LiAlH4, or LiAlH4/AlCl3.


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