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Synlett 1999; 1999(2): 225-227
DOI: 10.1055/s-1999-2581
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4-Acetoxy- and 4-Triflyloxy-2,6,6-trimethyl-2,4-cyclohexadienones as Nondimerizing Alternatives to 2,6,6-Trimethyl-2,4-cyclohexadienone. Efficient Synthesis of Several Bicyclo[2.2.2]octenone Derivatives

Ming-Shyong Yang* , Shi-Yi Chang, Shyue-Sheng Lu, Polisetti Dharma Rao, Chun-Chen Liao
  • *Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 300; Fax +8 86-3-5 71 10 82; E-mail: ccliao@faculty.nthu.edu.tw
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Publication Date:
31 December 1999 (online)

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4-Acetoxy- and 4-trifyloxy-2,6,6-trimethyl-2,4-cyclohexadienones were employed as non-dimerizing alternatives to 2,6,6-trimethyl-2,4-cyclohexadienone in Diels-Alder reactions with substituted acetylenes which facilitated the synthesis of substituted bicyclo[2.2.2]octen-2,5-diones, bicyclo[2.2.2]octadienones and 5-methylenebicyclo[2.2.2]octen-2-ones.

2,4-cyclohexadienones - Diels-Alder reactions - vinyl triflates - bicyclo[2.2.2]octendiones - bicyclo[2.2.2]octadienones