Maji, Manasi and Mallick, Dibyendu and Mondal, Sayantan and Anoop, Anakuthil and Bag, Subhendu Sekhar and Basak, Amit and Jemmis, Eluvathingal D (2011) Selectivity in Garratt-Braverman Cyclization: An Experimental and Computational Study. In: Organic Letters, 13 (5). pp. 888-891.
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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:||Journal Article|
|Additional Information:||Copyright of this article belongs to American Chemical Society.|
|Department/Centre:||Division of Chemical Sciences > Inorganic & Physical Chemistry|
|Date Deposited:||18 Mar 2011 10:40|
|Last Modified:||18 Mar 2011 10:40|
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