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Beckmann Rearrangements of 1-Indanone Oxime Derivatives Using Aluminum Chloride and Mechanistic Considerations
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  • Beckmann Rearrangements of 1-Indanone Oxime Derivatives Using Aluminum Chloride and Mechanistic Considerations
  • Beckmann Rearrangements of 1-Indanone Oxime Derivatives Using Aluminum Chloride and Mechanistic Considerations
저자명
이병세,추소영,이인영,이본수,송중의,지대윤,Lee. Byeong Se,Chu. So Yeong,Lee. In Yeong,Lee. Bon Su,Song. Jung Ui,Ji. Dae Yun
간행물명
Bulletin of the Korean Chemical Society
권/호정보
2000년|21권 9호|pp.860-866 (7 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

Hydrocarbostyril, which is a key intermediate in our new synthetic route to 6-nitroquipazine, can be prepared from 1-indanone oxime by Beckmann rearrangement. We have optimized the reaction by using a Lewis acid, aluminum chloride,in the yield of 91% instead of common acids such as polyphosphoric acid,and sulfuric acid used in conventional Beckmann rearrangement (20% in the literature, 10% in our experiment).The optimized condition is established by usingthree equivalents of aluminum chloride in CH2Cl2 at -40 $^{circ}C$ - room tempera-turefor 40 min. We have applied this condition to other 1-indanone derivatives, such as 4-methyl-, 4-methoxy-, 4-nitro and 6-nitro-1-indanones. The mechanism ofthis BR has been proposed on the basis of the effect of tem-perature and substituenton product ratio, with the aid of PM3 calculation for a model system.