Ruthenium Catalyzed Synthesis of N-Substituted Perhydroazepine Derivatives 


Vol. 34,  No. 6, pp. 652-657, Dec.  1990


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  Abstract

각종 일차아민과 1,6-헥산디올을 촉매량의 RuCl3·3H2O와 PR3의 존재하 180℃에서 5시간 반응시켜 N-치환 과수소아제핀을 높은 수득률로 얻었다. 방향족 아민인 아닐린 유도체에 대해서는 RuCl3·3H2O와 PR3을 이용한 촉매계가 적당하고, 한편으로 지방족 아민에 대해서는 RuCl3·3H2O와 PBu3을 이용한 촉매계가 효과적인 것으로 확인되었다. 이러한 차이점은 염기성이 작은 방향족 아민에 대해서는 염기성이 작은 포스핀 배위자인 PPh3가 유용하고 염기성이 큰 지방족아민에 대해서는 염기성이 큰 포스틴 배위자인 PBu3가 유용함을 알 수 있었다. Primary amines react with 1,6-hexanediol at 180℃ for 5 h under argon atmosphere in the presence of both RuCl3·3H2O and PR3 to give N-substituted perhydroazepine derivatives in good yields. For aromatic amines such as anilines, RuCl3·3H2O combined with PPh3 showed the highest catalytic activity. On the other hand, in the reaction of aliphatic amines, RuCl3·3H2O combined with PBu3 showed the highest catalytic activity. These differences may be attributed to the difference in the basicity of these amines. Less basic aromatic amines may require less basic phosphines, while more basic aliphatic amines may require more basic phosphines as the ligands.

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  Cite this article

[IEEE Style]

S. C. Shim, C. H. Doh, S. Y. Lee, W. H. Cho, K. T. Huh, "Ruthenium Catalyzed Synthesis of N-Substituted Perhydroazepine Derivatives," Journal of the Korean Chemical Society, vol. 34, no. 6, pp. 652-657, 1990. DOI: .

[ACM Style]

Sang Chul Shim, Chil Hoon Doh, Sung Yub Lee, Wan Ho Cho, and Keun Tae Huh. 1990. Ruthenium Catalyzed Synthesis of N-Substituted Perhydroazepine Derivatives. Journal of the Korean Chemical Society, 34, 6, (1990), 652-657. DOI: .

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ISSN(Print) 1017-2548
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