Simplified Procedures for 1-Amino-2-propyne and Some Homologues

Jan W. Zwikker; Lambert Brandsma; Hermann D. Verkruijsse

doi:10.1055/s-2003-42401

PSP

Simplified Procedures for 1-Amino-2-propyne and Some Homologues

Jan W. Zwikker^a, Lambert Brandsma*^b, Hermann D. Verkruijsse^c
^a Department of Physical Organic Chemistry, University of Utrecht, Padualaan 8, 3584 CH Utrecht, The Netherlands
^b Julianalaan 273, 3722-GN, Bilthoven, The Netherlands
e-Mail: l.brandsma@wxs.nl;
^c Department of Chemical Education, Sorbonnelaan 16, 3584 CH Utrecht, The Netherlands

Abstract

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Abstract

1-Amino-2-propyne has been obtained in good yields by successive solvolysis of propargyl bromide in liquid ammonia, metalation of the dissolved amine with sodamide, and hydrolysis after complete removal of the ammonia by evaporation. Some homologues, RC≡CCH₂NH₂, have been obtained in fair yields by addition of alkyl bromides to the solution of the sodium derivative of 1-amino-2-propyne.

Key words

aminations - amines - alkynes - metalations - alkylations

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References

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Brandsma, L. Synthesis of Acetylenes, Allenes, and Cumulenes, Methods and Techniques, Elsevier, to appear in 2003 or 2004.