Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Hydroiminoacylation of $\alpha,\omega$-diene with Aldimine by Rh(Ⅰ) and Isomerization of the Terminal Olefin to the Internal Olefin

  • Published : 1993.04.20
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Abstract

Catalytic iminohydroacylation has been achieved by the reaction of aldimine 1 and 1,5-hexadiene (2a) with Wilkinson's complex as catalyst. Compounds 7a, 8a and 9a were obtained as final product after hydrolysis of the resulting iminohydroacylation products 4a, 5a and 6a. Depending on the reactant ratio (2/1), the ratio of products were changed dramatically : As the 2/1 ratio was increased, 7a is the major product after hydrolysis while 8a is the major with an 1/1 ratio of 2/1. The mechanism of the formation of 5a is determined by the reaction of 1 and 2b under the identical reaction conditions. Considering that 5a may not be formed from the hydroiminoacylation of 14a since 5b cannot be formed from that of conjugate diene 14b generated from isomerization of 2b, 5a must be formed from the reaction of 4a and 10 by addition-elimination mechanism.

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