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Selectivity in Garratt-Braverman Cyclization: An Experimental and Computational Study

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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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol102861j


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
Publication: Organic Letters
Publisher: American Chemical Society
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
URI: http://eprints.iisc.ac.in/id/eprint/35989

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