Differential reactivity of 3H-indole styrylcyanines: Intermolecular [4π + 2π] cycloaddition vs. proton - shift coupled six - electron electrocyclization. Issue 24 (14th June 2018)

• Record Type: Journal Article
• Authors: Thottiparambil, Abhineeshbabu; Purushothaman, Indu; De, Susmita; Parameswaran, Pattiyil; Beegum, P. Shifana; Antharjanam, P.K. Sudhadevi; Chakkumkumarath, Lakshmi
• Is Part Of: Tetrahedron. Volume 74:Issue 24(2018)
• Page Start: 2999
• Page End: 3006
• Publication Date: 2018-06-14
• Subjects: Styrylcyanines -- Homo - dimerization -- Electrocyclization -- [3, 3, 1] oxazabicyclononanes -- N-alkenyl spiropyrans; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.04.085
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Differential reactivity of 3 H -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 N H -spiropyran dictates the differential reactivity and the initial step for both reactions is a six-membered ring formation via six - electron pericyclic reactions. Graphical abstract: Differential reactivity of 3 H -indole styrylcyanines leading to oxazabicyclo[3, 3, 1]nonanes or N -alkenyl spiropyrans is reported.