AI Article Synopsis
- The study investigates how silicon affects the stability of a cation and radical in 2-azetidinone systems using NMR kinetics.
- The silicon substituent has little to no impact on the cation's stability but shows a slight enhancement for the radical.
- The findings suggest that antiaromaticity significantly reduces the beta-stabilizing effect of silicon.
Article Abstract
The beta-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 beta-effect is virtually nonexistent in the case of a cation, a foiled beta-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 beta-stabilizing effect of silicon.
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| http://dx.doi.org/10.1021/ol902411r | DOI Listing |
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