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The low yield is probably due to the low reactivity of 1-chloroanthraquinone 4a, because quenching experiments of 3a with methyl iodide under the same reaction conditions delivered 1-methoxy-6-(tetrahydropyran-2-yloxy)hexane in 80% yield.
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According to recent results by Wortmann, complexes of donor substituted aromatic systems and quinones display charge transfer absorptions at 346 nm. R. Wortmann, personal communication.
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73
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Charge transfer complexes of 6 with stronger acceptors such as TNF gave absorptions at 496 nm and 600 (sh) nm according to Markovitsi. See refs. 15 and 28 for details.
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74
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33646034501
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Becher has shown that a very weak charge-transfer absorption in the UV spectrum could only be observed after keeping a solution of the donor acceptor complex for several days. See ref. 35 for details.
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W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.
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(1978)
J. Org. Chem.
, vol.43
, pp. 2923
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Still, W.C.1
Kahn, M.2
Mitra, A.3
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