Photoinduced electron transfer cyclizations of aryl-linked phthalimides

…, DH Ahn, KS Lee, AR Kim, DJ Yoo, M Oelgemöller

Index: Lee, Yong-Jun; Ahn, Do-Hwan; Lee, Kyoung-Sub; Kim, Ae Rhan; Yoo, Dong Jin; Oelgemoeller, Michael Tetrahedron Letters, 2011 , vol. 52, # 39 p. 5029 - 5031

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Citation Number: 9

Abstract

The photochemistry of arene-linked phthalimides incorporating the carboxylate or thioether donor group was investigated. Simple N-phthalimidophenyl alkanoates exclusively gave photoreduction (CO2H/H-exchange) products. In contrast, ω-phthalimido-meta-phenoxy carboxylates underwent photodecarboxylative cyclizations in yields of 6–48%. Likewise, catechol-linked derivatives furnished analogue cyclization products in 18–38% yield. ...