Maji, Manasi ; Mallick, Dibyendu ; Mondal, Sayantan ; Anoop, Anakuthil ; Bag, Subhendu Sekhar ; Basak, Amit ; Jemmis, Eluvathingal D. (2011) Selectivity in Garratt-Braverman cyclization: an experimental and computational study Organic Letters, 13 (5). pp. 888-891. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol102861j
Related URL: http://dx.doi.org/10.1021/ol102861j
Abstract
Bispropargyl sulfones equipped with aromatic rings of dissimilar nature were synthesized. Under basic conditions, these sulfones isomerized to the bisallenic sulfones, creating a competitive scenario between two alternate Garratt-Braverman (GB) cyclization pathways. The observed product distribution ruled out the involvement of any ionic intermediate and supported the diradical mechanism with greater involvement of the electron-rich aromatic ring via the more nucleophilic radical. DFT-based calculations supported the diradical mechanism along with the observed selectivity.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 82715 |
| Deposited On: | 14 Feb 2012 11:48 |
| Last Modified: | 13 Jul 2012 11:39 |
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