Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Electrolytic Synthesis of 9-Methyl-2,3,6,7-tetramethoxyfluorene with Carbon Electrodes

카본전극을 이용한 9-Methyl-2,3,6,7-tetramethoxyfluorene의 합성

  • Kim, Duk-Hyun (Dept. of Industrial Chemistry, Chungnam Sanup University)
  • 김덕현 (충남산업대학교 공업화학과)
  • Received : 1996.08.09
  • Accepted : 1996.12.26
  • Published : 1997.02.10
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Abstract

The intramolecular cyclization of 1,1-bis-(3,4-dimethoxyphenyl)ethane was shown to take place upon anodic oxidation at carbon electrodes in acetonitrile or in a solvent-mixture containing dichloromethane, trifluoroacetic acid(TFA). Yields are low in the former solvent due to the fact that the cyclized product (9-methyl-2,3,6,7-tetramethoxyfluorene) is more easily oxidized than it's precursor and the oxidation product is not stable. In the presence of TFA, the cation radical derived from the oxidation of the cyclized product is stabilized thus, after reduction may be isolated with better yields.

카본전극을 이용한 양극산화을 통해 1,1-Bis-(3,4-dimethoxyphenyl)ethane으로부터 $CH_3CN$이나 $CH_2Cl_2/TFA$-혼합용액계에서 Intramolecular cyclizatlon 반응이 일어났다. Intramolecular cyclization에 의한 생성물(9-methyl-2,3,6,7-tetramethoxyfluorene)은 출발물질보다 더 쉽게 산화되고, 그에 따른 산화생성물은 $CH_3CN$계에서 불안정하여 낮을 수율을 나타냈다. TFA가 존재하는 계에서는 Fluorene 유도체의 산화생성물인 radical cation이 안정하여 환원 후에 더 좋은 수율로 합성할 수 있었다.

Keywords

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