461389-75-3Relevant academic research and scientific papers
Electron-Withdrawing β-Substituent, Ring-Strain, and Ortho Effects on Reactivity, Selectivity, and Stability of o-Alkoxybenzyl Carbocations
Tseng, Meng-Yun,Hung, Hsin-Yi,Sung, Kuangsen
, p. 3905 - 3912 (2015)
o-Alkoxybenzyl carbocations 1 and 2 were generated by laser flash photolysis of the corresponding o-alkoxybenzyl alcohols 3 and 4 to understand how the electron-withdrawing β-substituent, the ring-strain, and the ortho effects affect the reactivity (electrophilicity), selectivity, and stability of 1 and 2, and to fit the electrophilicity of 1 and 2 into the current carbocation electrophilicity scale (E). Our finding is that both the electron-withdrawing β-substituent and the ring-strain effects make 1 less stable than 2 by 3.0 kcal/mol. These effects plus the ortho effect of 2 make 1 more reactive than 2, but the selectivity of 1 and 2 toward amine nucleophiles is almost the same within experimental errors. The electrophilicity of 1 and 2 has been fit into the current carbocation electrophilicity scale (E) quite well. (Chemical Equation Presented).
Iron-catalyzed intermolecular hydroamination of styrenes
Huehls, C. Bryan,Lin, Aijun,Yang, Jiong
supporting information, p. 3620 - 3623 (2014/08/05)
An iron-catalyzed formal hydroamination of alkenes has been developed. It features O-benzoyl-N,N-dialkylhydroxylamines as the electrophilic nitrogen source and cyclopentylmagnesium bromide as the reducing agent for intermolecular hydroamination of styrene
