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KMID : 1059519900340050490
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Journal of the Korean Chemical Society
1990 Volume.34 No. 5 p.490 ~ p.497
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Synthesis and Properties of 1,4-Diboracyclohexene-2 Derivatives
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Uhm Jae-Kook
Hu D,
Zenneck U.
Pritzkow W.
Siebert W,
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Abstract
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Two synthetic routes for the 1,4-diboracyclohexene-2 ring 8 have been developed. Method i) starts with 1,2-bis(dichloroaluminyl)ethane, in which the AlCl2 group is replaced by BCl2. Exchange of the chlorine with BI3 in 1,2-bis-(dichloroboryl)ethane yields the corresponding iodo compound, which reacts with the alkynes to heterocycles 8a, b in good yield. In method ii) B2Cl4 is added to alkenes, replacement of chlorine with BI3 yields the bis(diiodoboryl)ethane derivatives which undergo redox reactions with alkynes to give 8c, d. The diiodo derivative 8a forms the pyridine adduct 9a, and reacts with ether to give the ethoxy derivative 8f. 8a-d react with AlMe3 to yield the corresponding dimethyl derivatives 8g-j, which give unstable radical anions when treated with potassium in THF. The ESR parameters are reported. In electrochemical experiments irreversible reductions of 8g-j are observed. 8g-j react with (C5H5)Co(C2H4)2 to give the intermediate 16 VE complexes (C5H5)Co(8), in which C-H activation occurs with formation of the corresponding red 1,4-diboracyclohexadiene complexes 10. The X-ray structure analyses of 10h and 10j are reported.
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