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Differential reactivity of 3H-indole styrylcyanines: Intermolecular [4Ï€ + 2Ï€] cycloaddition vs. proton - shift coupled six - electron electrocyclization
Date Issued
14-06-2018
Author(s)
Thottiparambil, Abhineeshbabu
Purushothaman, Indu
De, Susmita
Parameswaran, Pattiyil
Beegum, P. Shifana
Antharjanam, P. K.Sudhadevi
Chakkumkumarath, Lakshmi
Abstract
Differential reactivity of 3H-indole styrylcyanines leading to oxazabicyclo[3,3,1]nonanes or N-alkenyl spiropyrans is reported. Quantum mechanical calculations show that the isomerization of styrylcyanine to NH-spiropyran dictates the differential reactivity and the initial step for both reactions is a six-membered ring formation via six - electron pericyclic reactions.
Volume
74