17424-79-2Relevant articles and documents
Understanding α,β-unsaturated imine formation from amine additions to α,β-unsaturated aldehydes and ketones: An analytical and theoretical investigation
Calow, Adam D. J.,Carbó, Jorge J.,Cid, Jessica,Fernández, Elena,Whiting, Andrew
supporting information, p. 5163 - 5172 (2014/06/23)
A combination of in situ IR spectroscopy (ReactIR) and DFT calculations have been used to understand what factors govern the selectivity in the addition of primary amines to α,β-unsaturated aldehydes and ketones, i.e., 1,2- versus 1,4-addition. It has been found that the 1,2-addition products (α,β-unsaturated imines following addition and elimination) usually predominate for most systems. However, exceptions, such as methyl vinyl ketone, selectively give 1,4-addition products. This has been rationalized by DFT calculations that show that major conformational effects are involved, controlled mainly by steric effects of carbonyl substituents, resulting in a model that provides simple and predictable preparation of α,β- unsaturated imines for in situ utilization in synthesis.
Halogenated Ketenes. 38. Cycloaddition of α,β-Unsaturated Imines with Ketenes To Yield Both β- and δ-Lactams
Brady, William T.,Shieh, C. H.
, p. 2499 - 2502 (2007/10/02)
The cycloaddition of various types of α,β-unsaturated imines with diphenyl- and dichloroketenes yields both (2 + 2) and (4 + 2) cycloaddition products, i. e., β-lactams and δ-lactams, respectively.The cycloaddition products are dependent upon substitution in the imine and the ketene.The δ-lactams derived from dichloroketene are easily dehydrochlorinated to the corresponding 2-pyridones.All of the results are consistent with a two-step cycloaddition process involving a dipolar intermediate.
