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P. Dowd and S.-C. Choi, “Free Radical Ring Expansion and Rearrangement of Large Carbocyclic Rings,” Tetra-hedron Letters, Vol. 32, No. 5, 1991, pp. 565-568. doi:10.1016/S0040-4039(00)74828-3

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• TITLE: Eco-friendly Synthesis of Cyclododecanone from Cyclododecatriene

  AUTHORS: Qi Feng, De-Kai Yuan, Dao-Quan Wang, Xiao-Mei Liang, Jian-Jun Zhang, Jin-Ping Wu, Fu-Heng Chen

  KEYWORDS: Eco-Friendly Synthesis, Cyclododecanone, Cyclododecatriene, Hexadecyl Trimethyl Ammonium Heteropolyphosphatotungstate

  JOURNAL NAME: Green and Sustainable Chemistry, Vol.1 No.3, August 31, 2011

  ABSTRACT: An eco-friendly synthesis of cyclododecanone (CDON) from cyclododecatriene (CDT) is described. Selec- tive epoxidation of CDT with hydrogen peroxide using hexadecyl trimethyl ammonium heteropolyphospha- totungstate [(n-C16H33NMe3)3PW4O16, HAHPT] as catalyst and water as solvent followed by the hydrogena- tion on Raney nickel catalyst gave cyclododecanol (CDOL). The latter was oxidized with hydrogen peroxide using HAHPT as catalyst and a mixture of water and t-butanol as solvent to afford CDON. The total yield was 53.4% under the optimum reaction conditions.