Beckmann Rearrangement of Ring A Steroidal Oxime Using the Carbon tetrachloride-triphenylphosphine 


Vol. 23,  No. 1, pp. 42-45, Feb.  1979


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  Abstract

벡크만 자리옮김반응의 실험조건은 대부분이 센산 (HCl, H2SO4, PCl5등)이나, 고온과 같은 격렬한 반응조건을 사용하므로 이러한 조건은 자주 전위보다는 케토옥심의 이성질화를 일으킨다. 5α-cholestan-3-one oxime의 벡크만 전위에 온화하고 중성의 조건인 사염화탄소와 트리페닐포스핀을 사용하여 3-aza-A-homo-5α-cholestan-4-one을 얻었다. 이러한 새롭고, 온화하며 쉽고 빠른 베그만 전위를 소개하고 이러한 방법을 고전적인 벡크만 전위 시약인 폴리인산을 사용한 방법과 비교하였다. The experimental procedures of Beckmann rearrangement mostly involve the use of vigorous conditions such as strongly acidic reagents (conc. HCl, H2SO4, PCl5, etc.) or elevated temperatures, which frequently cause isomerization of ketooximes prior to rearrangement.We have effected the Beckmann rearrangement on 5α-cholestan-3-one oxime using the carbon tetrachloride-triphenylphosphine reagent under mild, neutral conditions to give 3-aza-A-homo-5α-cholestan-4-one. This new, mild, facile and rapid general method of Beckmann rearrangement is presented, and compared with the classical (more conventional) Beckmann reagent of polyphosphoric acid.

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  Cite this article

[IEEE Style]

J. C. Kim, S. Choi, W. Park, Y. Lee, "Beckmann Rearrangement of Ring A Steroidal Oxime Using the Carbon tetrachloride-triphenylphosphine," Journal of the Korean Chemical Society, vol. 23, no. 1, pp. 42-45, 1979. DOI: .

[ACM Style]

Jack C. Kim, Soon-kyu Choi, Won-Woo Park, and Yong-Tae Lee. 1979. Beckmann Rearrangement of Ring A Steroidal Oxime Using the Carbon tetrachloride-triphenylphosphine. Journal of the Korean Chemical Society, 23, 1, (1979), 42-45. DOI: .

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ISSN(Print) 1017-2548
ISSN(Online) 2234-8530