Beckmann rearrangements of 1-indanone oxime derivatives using aluminum chloride and mechanistic considerations

Title
Beckmann rearrangements of 1-indanone oxime derivatives using aluminum chloride and mechanistic considerations
Authors
Lee, B.S.; Chi, D.Y.
Keywords
Hydrocarbostyril
Issue Date
2000-09
Publisher
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
Abstract
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 using three equivalents of aluminum chloride in CH2Cl2 at -40 degrees C - room temperature for 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 of this BR has been proposed on the basis of the effect of temperature and substituent on product ratio, with the aid of PM3 calculation for a model system.
URI
http://dspace.inha.ac.kr/handle/10505/20174
ISSN
0253-2964
Appears in Collections:
College of Natural Science(자연과학대학) > Chemistry (화학) > Journal Papers, Reports(화학 논문, 보고서)
Files in This Item:
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