Photoinduced electron transfer cyclizations of aryl-linked phthalimides

Lee, Yong-Jun, Ahn, Do-Hwan, Lee, Kyoung-Sub, Kim, Ae Rhan, Yoo, Dong Jin, and Oelgemöller, Michael (2011) Photoinduced electron transfer cyclizations of aryl-linked phthalimides. Tetrahedron Letters, 52 (39). pp. 5029-5031.

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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. Using the photodecarboxylation protocol, macrocyclic target compounds with ring sizes up to 17 could thus be realized. Two model phthalimides containing a thioether branch at the ortho-position of the arene-linker gave the analogue seven-membered cyclization products in yields of 28% and 35%, respectively.

Item ID: 18292
Item Type: Article (Research - C1)
ISSN: 1873-3581
Keywords: photodecarboxylation; phthalimide; photoinduced electron transfer; photochemistry; photocyclization
Date Deposited: 29 Sep 2011 03:51
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 50%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 50%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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