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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 37, Number 2
JKCSEZ 37(2)
April 20, 1993 

Synthesis of Dinitro α,ω-Diols from α,ω-Diols

α,ω-디올로부터 디니트로 α,ω-디올의 합성
Kyoo-Hyun Chung, Il-Gyo Park

정규현, 박일교
니트로 알코올은 브로모 알코올의 치환반응으로 얻었다. 두번째 니트로 원자단은 사슬 길이에 따라 다른 방법으로 도입했다. 3,3-dinitro-1-propanol은 분자내 염기성 니트로화 반응으로 형성되면 5,5-dinitro-1-pentanol은 산화촉매 니트로화 반응으로 얻었다. 3,3-dinitro-1,6-hexanediol과 4,4-dinitro-1,8-octanediol은 3,3-dinitro-1-propanol과 5,5-dinitro-1-pentanol에 acrolein을 가해 Michael 반응으로 알데히드를 얻고 환원하여 합성했다. 치환반응시 알코올 보호기는 아세틸기가 좋으며 산화촉매 니트로 반응에서는 THP 원자단이 좋은 보호기이다.

Nitroalcohols were prepared by a substitution reaction from the corresponding bromoalcohols. The second nitro group was introduced via different methods depending on the carbon chain length. 3,3-Dinitro-1-propanol was obtained by an intramolecular varient of the alkaline nitration method. Whereas 5,5-dinitro-1-pentanol was given by the catalytic oxidative nitration. 3,3-Dinitro-1-propanol and 5,5-dinitro-1-pentanol were converted to 3,3-dinitro-1,6-hexanediol and 4,4-dinitro-1,8-octanediol via Michael reaction with acrolein followed by the reduction of the resulting aldehydes. Acetyl group was a good protecting group for the substitution reaction while THP was for the catalytic oxidative nitration.

244 - 248
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