Chemistry:Cyclobutylamine

From HandWiki

Cyclobutylamine is an organic compound with the formula C
4
H
7
NH
2
. It is a colorless, readily distillable liquid. It can be prepared from cyclobutanecarboxylic acid via the amide or by Curtius rearrangement.[1] Cyclobutylamine is a member of the aminocycloalkanes, which also includes cyclopropylamine, cyclopentylamine, and cyclohexylamine.

Oxidation with potassium permanganate gives cyclobutanone.[2]

Using "strain-relief reaction", substituted bicyclobutanes can be converted to a variety of N-substituted cyclobutylamines.[3]

References

  1. Newton W. Werner, Joseph Casanova, Jr. (1967). "Cyclobutylamine". Organic Syntheses 47: 28. doi:10.15227/orgsyn.047.0028. 
  2. Lee, Donald G.; Ribagorda, María; Adrio, Javier (2007). "Potassium Permanganate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rp244.pub2. ISBN 978-0-471-93623-7. 
  3. Gianatassio, Ryan; Lopchuk, Justin M.; Wang, Jie; Pan, Chung-Mao; Malins, Lara R.; Prieto, Liher; Brandt, Thomas A.; Collins, Michael R. et al. (2016). "Strain-release amination". Science 351 (6270): 241–246. doi:10.1126/science.aad6252. PMID 26816372. Bibcode2016Sci...351..241G.