Light mediated reaction provides a versatile method to access complex molecule as it involves multiple bond formation in a single step. [2+2] photocycloaddition reaction is one such reaction, which provides access to a strained four membered ring. However, Imine mediated [2+2] photocycloaddition is difficult to achieve as excitation of imine leads to various deactivation pathways. To direct the reactivity of imines towards [2+2]-photocycloaddtion known as the Aza Paternò- Büchi reaction, molecular design targeting the control of excited state pathways becomes necessary. Recently we demonstrated that an intramolecular Paternò-Büchi type reaction of enamide tethered with carbonyl group where enamide undergoes excitation is feasible called the transposed Paternò- Büchi reaction. This inspired us to design enamide tethered with imine and see whether cycloaddition is possible to achieve. The presentation highlights such reactivity of imine and their photophysical studies to understand the mechanism of reaction.

Realizing Aza Paternò-Büchi reaction

254th National Meeting (2017)

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