Chemoselective Photoreaction of Enamides: Divergent Reactivity towards [3+2]-Photocycloaddition vs Paternò-Büchi Reaction

Sunil Kumar Kandappa; Elango Kumarasamy; Ravichandranath Singathi; Lakshmy Kannadi Valloli; Angel Ugrinov; Jayaraman Sivaguru

doi:10.1111/php.13489

Chemoselective Photoreaction of Enamides: Divergent Reactivity towards [3+2]-Photocycloaddition vs Paternò-Büchi Reaction

Photochem Photobiol. 2021 Nov;97(6):1391-1396. doi: 10.1111/php.13489. Epub 2021 Aug 20.

Authors

Sunil Kumar Kandappa^{1

2}, Elango Kumarasamy^{1

3}, Ravichandranath Singathi¹, Lakshmy Kannadi Valloli¹, Angel Ugrinov⁴, Jayaraman Sivaguru¹

Affiliations

¹ Center for Photochemical Sciences and Department of Chemistry, Bowling Green State University, Bowling Green, OH, USA.
² Department of Chemistry, University of Southern California, Los Angeles, CA, USA.
³ Conamix Inc, Ithaca, NY, USA.
⁴ Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, USA.

PMID: 34287915
DOI: 10.1111/php.13489

Abstract

Photoreaction of enamides tethered to a phenyl ketone leads to either [3+2]-photocycloaddition or Paternò-Büchi reaction. This divergence in chemical reactivity originating from the same excited state was dependent on the reaction temperature. At low temperatures the Paternò-Büchi reaction was preferred, whereas at higher temperatures there was preference toward formation of [3+2]-photoproduct.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Temperature*