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

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

• 1 Gloset C. Coupe R. Bull. Soc. Chim. Fr.  1963,  2464 
• 2 Marszak L. Koulkes M. Bull. Soc. Chim. Fr.  1956,  93  and references mentioned therein
• 3 Marszak-Fleury A. Ann. Chim. (Paris, France)  1958,  3:  656 
• 4 Koziara A. Zwierzak A. Synthesis  1992,  1063 
• 5 Klepacz A. Zwierzak A. Synth. Commun.  2001,  1683 
• 6 Zwierzak A. Synth. Commun.  2001,  2287 
• 7 Koziara A. Zawadski S. Zwierzak A. Synthesis  1985,  202 
• 8 Brandsma L. Preparative Acetylenic Chemistry   Elsevier; Amsterdam: 1988.  p.2nd. ed. 

9

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