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■ Photolysis of Dimethyl 2-Diazo-6-oxo-2,6-dihydroazulene-1,3-dicarboxylate and Methyl 3-Cyano-2-diazo-6-oxo-2,6-dihydroazulene-1-carboxylate in Tetrahydrofuran

Shih-Jue Lin, Shuan-Ya Jiang, Tian-Chyuan Huang, Ping Kao, Pai-Feng Tsai, Hitoshi Takeshita, Yun-Shan Lin,* and (the late) Tetsuo Nozoe

*Department of Chemistry, Tamkang University, Tamsui, 25137, Taiwan, R.O.C.

Abstract

Upon photolysis in tetrahydrofuran, dimethyl 2-diazo-6-oxo-2,6-dihydroazulene-1,3-dicarboxylate afforded a crown-type origomerized cyclic ether in very low yield, but the major products were the C-H insertion products such as 2,6-disubstituted azulenedicarboxylate, whereas methyl 3-cyano-2-diazo-6-oxo-2,6-dihydroazulene-1-carboxylate gave, similar to 1,3-dicyano-2-diazo-2,6-dihydroazulen-6-one, oligomeric crown ethers predominantly, suggesting that a steric factor played a crucial role in their formations.