865486-22-2Relevant academic research and scientific papers
Suppressed β-effect of silicon in 3-silylated monocyclic β-lactams: The role of antiaromaticity
Bag, Subhendu Sekhar,Kundu, Rajen,Basak, Amit,Slanina, Zdenek
, p. 5722 - 5725 (2009)
[Chemical Equation Presented] The β-stabilizing effect of silicon substituent at C-3 on a C-4 cation and a radical In the 2-azetidinone systems is studied using NMR kinetics. While the β-effect Is virtually nonexistent in the case of a cation, a foiled β-effect (only a 3-fold rate enhancement) Is observed for a radical intermediate. From both the experimental and theoretical studies, It Is demonstrated that antiaromaticity Is playing the prime role In suppressing the β-stabilizing effect of silicon.
