18369-96-5Relevant articles and documents
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Hennion,Teach
, p. 1653 (1953)
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REACTIONS OF NITROGEN NUCLEOPHILES WITH 1-BROMOALLENES: REGIOSELECTIVE SYNTHESIS OF PROPARGYLAMINES
Geri, Roberto,Polizzi, Carmela,Lardicci, Luciano,Caporusso, Anna Maria
, p. 241 - 248 (2007/10/02)
The results of a study on the reactivity of 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes 2 towards nitrogen nucleophiles, such as aqueous ammonia, lithium amide, aliphatic and aromatic amines allowed us to propose new methods for the synthesis of propargylamines, 1, with an available acetylenic hydrogen.The regio- and the stereoselectivity of these reactions are examined and possible mechanisms are discussed.
Preparation of a Series of Highly Hindered Secondary Amines, Including Bis(triethylcarbinyl)amine
Kopka, Ihor E.,Fataftah, Zacharia A.,Rathke, Michael W.
, p. 4616 - 4622 (2007/10/02)
A series of highly branched secondary amines was prepared by coupling propargylamines with propargyl chlorides.Hydrogenation of the resultant dipropargylamines was accomplished with Raney nickel in the presence of potassium hydroxide.The resultant amines, including bis(triethylcarbinyl)amine, are among the most hindered secondary amines reported to date.The pKa values of the conjugate acids of the series of secondary amines exhibit a regular decrease with increasing size of the amine.The bulkier members of the series are inert to methyl iodide.Bis(triethylcarbinyl)amine reacts with boron trifluoride etherate to give a primary amine adduct and 3-ethyl-2-pentene.