61692-98-6Relevant academic research and scientific papers
CuI-catalyzed cross-coupling of N-tosylhydrazones with terminal alkynes: Synthesis of 1,3-disubstituted allenes
Hossain, Mohammad Lokman,Ye, Fei,Zhang, Yan,Wang, Jianbo
, p. 1236 - 1241 (2013/04/10)
A CuI-catalyzed synthesis of 1,3-disubstituted allenes from 1-alkynes by the reaction with various N-tosylhydrazones has been developed. This method, which uses readily available starting materials and is operationally simple, offers 1,3-disubstituted all
Gold-catalyzed highly enantioselective synthesis of axially chiral allenes
Lo, Vanessa Kar-Yan,Wong, Man-Kin,Che, Chi-Ming
, p. 517 - 519 (2008/09/19)
Axially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4 in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 °C. The reaction has been applied to the synthes
Electron Demand in the Transition State of the Cyclopropylidene to Allene Ring Opening
Warner, Philip,Sutherland, Robert
, p. 6294 - 6300 (2007/10/02)
The electronic structure of the transition state for the cyclopropylidene to allene conversion has been probed.The methodology involved the relative rates of ring opening vs trapping by MeOH for a series of variously substituted 2,3-diarylcyclopropylidenes.With the assumption that the rate of trapping was unaffected by substituents, a Hammett correlation was constructed.The negative value (-0.72) for ρ indicated that the carbenic center attracts electron density in the ring-opening transition state, much like the cyclopropyl cation to allyl cation transition state.Temperature-dependent studies showed that the observed preference for ring opening was driven by entropy factors.Also, using reasonable estimates for the close to diffusion-controlled trapping activation enthalpies, the derived enthalpies for ring opening were in close agreement with the best theoretical values.
