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0009740640
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note
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This observation is highly in contrast to those in the reactions reported by Tanner: addition of AIBN significantly increased the yields of reduced products, which was rationalized by the electron transfer induced radical chain mechanism.6
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4a,11
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41
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0009739064
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note
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The reaction did not smoothly proceed without DMPBI. For example, irradiation of BDMAP with 1o in the absence of DMPBI did not produce 2o at all. Apparently, decomposition of BDMAP was much more significant in this case than in the case using DMPBI. Therefore, DMPBI is necessary for the effective photosensitization reaction in which DMPBI may act as a reductant for the conversion of the cation radical of BDMAP to its neutral form.
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0009700649
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Aqueous THF as well as wet benzene were not effective solvent systems. On the other hand, the yield of 4 which was produced in non-aqueous MeCN was less than that in aqueous MeCN. Therefore, irradiation in aqueous polar solvents should be recommended for the reduction of simple aromatic ketones by DMPBI.
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49
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61
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0009710883
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note
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Spectral and elemental analysis data of epoxy ketones 1b, 1d, 1k, 11 and hydroxy ketones 2b, 2d, 2k, 21 were reported as Supplementary Material of reference 8k.
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DMPI was prepared by Mangeney's procedure: Mangeney, P., Gosmini, R., Raussou, S., Commercon, M., Alexakis, A. J. Org. Chem. 1994, 59, 1877. General procedure of protection of aldehydes by N, N'-dimethyl-1,2-ethylenediamine: Greene, T. W., Wuts, P. G. M. Protective Groups in Organic Synthesis: Wiley, New York, 1991: pp 218-219.
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DMPI was prepared by Mangeney's procedure: Mangeney, P., Gosmini, R., Raussou, S.,Commercon, M., Alexakis, A. J. Org. Chem. 1994, 59, 1877. General procedure of protection of aldehydes by N, N'-dimethyl-1,2-ethylenediamine: Greene, T. W., Wuts, P. G. M. Protective Groups in Organic Synthesis: Wiley, New York, 1991: pp 218-219.
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