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Synthesis 2003(15): 2427-2428  
DOI: 10.1055/s-2003-42401
PSP
© Georg Thieme Verlag Stuttgart · New York

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

Jan W. Zwikkera, Lambert Brandsma*b, Hermann D. Verkruijssec
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
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Publikationsverlauf

Received 16 June 2003
Publikationsdatum:
29. September 2003 (online)

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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

    References

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