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Paper | Regular issue | Vol 41, No. 12, 1995, pp.2665-2682
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7029
Efficient and Regioselective Photocyclization Reactions of N-[(ω-Trimethylsilylmethoxy)polyoxalkyl]phthalimides to Azacrown Ethers

Ung Chan Yoon*, Sun Wha Oh, and Chan Woo Lee

*Department of Chemistry, College of Natural Sciences, Pusan National University, Pusan 609-735, Korea


Single electron transfer induced photocyclization reactions of N-[(ω-trimethylsilylmethoxy)polyoxalkyl]phthalimides have been explored. Photocyclizations occur in methanol in modest to high yield to produce cyclized products in which phthalimide carbonyl carbon is bonded to the ω-carbon of side chain in place of the trimethylsilyl group. The efficient, chemoselective, and regioselective cyclization reactions represent synthetically useful processes for construction of azacrown ethers of various sizes.