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KMID : 1059519920360020301
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Journal of the Korean Chemical Society
1992 Volume.36 No. 2 p.301 ~ p.304
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The Facile Synthesis of Pyrrolidinobenzenes from Adipaldehyde and Phenylenediamine using HFe(CO)4-
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Shim Sang-Chul
Woo Byung-Won
Doh Chil-Hoon
Lee Dong-Yeob
Youn Young-Zoo
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Abstract
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Ethanolic tetracarbonylhydridoferrate, HFe(CO)4-, combined with adipaldehyde is very efficient for the selective transformation of an amino group into a perhydroazepine ring. Phenylenediamines react with adipaldehyde in the presence of HFe(CO)4- at room temperature under the atmospheric pressure of carbon monoxide to give the corresponding perhydroazepines in moderate yields. In these reactions, the molar ratio of 1.0 : 1.0 : 1.0 of the ferrate-adipaldehyde-phenylenediamine system gave one perhydroazepine ring, and the case of 1.0 : 2.0 : 1.0 gave two perhydroazepine rings, selectively.
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