Bag, Subhendu Sekhar ; Kundu, Rajen ; Basak, Amit ; Slanina, Zdenek (2009) Suppressed β-effect of silicon in 3-silylated monocyclic β-lactams: the role of antiaromaticity Organic Letters, 11 (24). pp. 5722-5725. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol902411r
Related URL: http://dx.doi.org/10.1021/ol902411r
Abstract
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 1778 |
| Deposited On: | 05 Oct 2010 12:02 |
| Last Modified: | 12 Jan 2011 11:14 |
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