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Volumn 55, Issue 45, 1999, Pages 12957-12968

Reductive transformation of α β-epoxy ketones and other compounds promoted through photoinduced electron transfer processes with 1,3-dimethyl- 2-phenylbenzimidazoline (DMPBI)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; EPOXIDE; HALIDE; HALOKETONE; IMIDAZOLINE DERIVATIVE; KETONE DERIVATIVE; RADICAL;

EID: 0033527812     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00804-2     Document Type: Article
Times cited : (131)

References (65)
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    • Fukuzumi, S.1
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    • (b) Applications of NADH analogues to PET reactions: Pac, C., Miyauchi, Y., Ishitani, O., Ihama, M., Yasuda, M., Sakurai. H. J. Org. Chem. 1984, 49, 26; Ishitani, O., Yanagida, S., Takamuku, S., Pac, C. J. Org. Chem. 1987, 52, 2790; Okada, K., Okubo, K., Morita, N., Oda, M. Chem. Lett. 1993, 2021.
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    • Pac, C.1    Miyauchi, Y.2    Ishitani, O.3    Ihama, M.4    Yasuda, M.5    Sakurai, H.6
  • 23
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    • (b) Applications of NADH analogues to PET reactions: Pac, C., Miyauchi, Y., Ishitani, O., Ihama, M., Yasuda, M., Sakurai. H. J. Org. Chem. 1984, 49, 26; Ishitani, O., Yanagida, S., Takamuku, S., Pac, C. J. Org. Chem. 1987, 52, 2790; Okada, K., Okubo, K., Morita, N., Oda, M. Chem. Lett. 1993, 2021.
    • (1987) J. Org. Chem. , vol.52 , pp. 2790
    • Ishitani, O.1    Yanagida, S.2    Takamuku, S.3    Pac, C.4
  • 24
    • 33845470010 scopus 로고
    • (b) Applications of NADH analogues to PET reactions: Pac, C., Miyauchi, Y., Ishitani, O., Ihama, M., Yasuda, M., Sakurai. H. J. Org. Chem. 1984, 49, 26; Ishitani, O., Yanagida, S., Takamuku, S., Pac, C. J. Org. Chem. 1987, 52, 2790; Okada, K., Okubo, K., Morita, N., Oda, M. Chem. Lett. 1993, 2021.
    • (1993) Chem. Lett. , pp. 2021
    • Okada, K.1    Okubo, K.2    Morita, N.3    Oda, M.4
  • 37
    • 0009740640 scopus 로고    scopus 로고
    • note
    • 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
  • 38
    • 0009749675 scopus 로고    scopus 로고
    • note
    • 8k
  • 40
    • 0009677121 scopus 로고    scopus 로고
    • note
    • 4a,11
  • 41
    • 0009739064 scopus 로고    scopus 로고
    • note
    • 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.
  • 43
    • 0000877912 scopus 로고
    • (a) Cohen, S. G., Baumgarten, R. J. J. Am. Chem. Soc. 1965, 87, 2996; 1967, 89, 3471.
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  • 47
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    • and references cited therin
    • (e) Recent example of the related reaction: Jones, P. B., Pollastri, M. P., Porter, N. A. J. Org. Chem. 1996, 61, 9445 and references cited therin.
    • (1996) J. Org. Chem. , vol.61 , pp. 9445
    • Jones, P.B.1    Pollastri, M.P.2    Porter, N.A.3
  • 48
    • 0009700649 scopus 로고    scopus 로고
    • note
    • 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.
  • 50
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    • (a) Dowd, P., Choi, S. C. J. Am. Chem. Soc. 1987, 109, 3493; 1987, 109, 6548.
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    • note
    • 18b
  • 61
    • 0009710883 scopus 로고    scopus 로고
    • note
    • 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.
  • 63
    • 0028365355 scopus 로고
    • 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.
    • (1994) J. Org. Chem. , vol.59 , pp. 1877
    • Mangeney, P.1    Gosmini, R.2    Raussou, S.3    Commercon, M.4    Alexakis, A.5
  • 64
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    • Wiley, New York
    • 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.
    • (1991) Protective Groups in Organic Synthesis , pp. 218-219
    • Greene, T.W.1    Wuts, P.G.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.