Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Dehydrogenation of 9,10-Dialkyl-9,10-dihydroanthracene with 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

2,3-디클로로-5,6-디시아노-1,4-벤조퀴논을 利用한 9,10-디알킬-9,10-디히드로안트라센 化合物의 수소이탈 반응

  • Wu-Lang Kim (Department of Chemistry, University of Illinois) ;
  • Moo-Jin Jun (Department of Applied Chemistry College of Engineering Kyungpook National University)
  • ;
  • 전무진 (경북대학교 공과대학 응용화학과)
  • Published : 1975.12.30
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Abstract

A series of 9,10-dialkyl-9,10-dihydroanthracene has been dehydrogenated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in good yields. The yield decreased with the larger alkyl groups in this 9,10-dialkyl-9,10-DHA series(DHA=dihydroanthracene). It is conceivable that trans-9,10-diisopropyl-9,10-DHA was dehydrogenated more rapidly than the cis-isomer, and, bassed on this observation, a concerted mechanism was ruled out and an ionic mechanism is proposed.

2,3-Dichoro-5,6-dicyano-1,4-benzoquinone을 이용하여 9,10-dialkyl-9,10-dihydroanthracene계열 화학물의 수소이탈 반응이 진행되었다. Alkyl기의 크기가 클 수록 수소이탈 반응의 수득률이 적어지며 트란스화합물이 시스화합물 보다 반응이 빨리 진행됨이 확인되었다ㅏ. 이들의 수소이탈 반응은 이온 메카니즘으로 설명되어진다.

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References

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