Selectivity in Garratt-Braverman cyclization: an experimental and computational study |
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| Authors: | Maji Manasi Mallick Dibyendu Mondal Sayantan Anoop Anakuthil Bag Subhendu Sekhar Basak Amit Jemmis Eluvathingal D |
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| Institution: | Department of Chemistry, Indian Institute of Technology, Kharagpur, India. |
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| 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. |
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