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KMID : 1059519930370110967
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Journal of the Korean Chemical Society
1993 Volume.37 No. 11 p.967 ~ p.973
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Ruthenium Complex Catalyzed Reaction of Diols or Triol with Amines
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Shim Sang-Chul
Youn Young-Zoo
Lee Jae-Wook
Lee Dong-Yeob
Shim Jae-Goo
Kim Ju-Hee
Huh Keun-Tae
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Abstract
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α,ω-Diols such as 1,6-hexanediol and 1,7-heptanediol react with secondary amines in the presence of catalytic amount of ruthenium complex at 180℃ for 24 hrs to give the corresponding diamino compounds in good yields. The yield of diamino compound was affected by the molar ratio of α,ω-diol to secondary amine. The reaction was also affected by the nature of the phosphorus ligands employed. On the other hand, aromatic primary amines react with 1,2,6-hexanetriol in the presence of RuCl3·H2O-3PPh3 at 180℃ for 3 hours under argon atmosphere to give selectively 1-substituted aryl-3-hydroxyperhydroazepines in good yields. Selective synthesis of these products show that two primary hydroxy groups (1,6-positions) oxidize predominantly than secondary hydroxy group (2-position) by ruthenium-phosphorus complex. The yields were decreased according to the order of para-, meta- and ortho-substituent.
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