메뉴 건너뛰기




Volumn 72, Issue 18, 2007, Pages 6961-6969

Alkenenitriles: Conjugate additions of alkyl iodides with a silica-supported zinc-copper matrix in water

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; COPPER; ELECTRON MICROSCOPY; SILICA; X RAY DIFFRACTION; ZINC;

EID: 34548738189     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0711539     Document Type: Article
Times cited : (17)

References (84)
  • 3
    • 33749365435 scopus 로고    scopus 로고
    • The Conjugate Addition Reaction
    • 2nd ed, Beller, M, Bolm, C, Eds, Wiley-VCH: Weinheim, Germany
    • Alexakis, A. The Conjugate Addition Reaction. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, pp 553-562.
    • (2004) Transition Metals for Organic Synthesis , vol.1 , pp. 553-562
    • Alexakis, A.1
  • 31
    • 33646444563 scopus 로고    scopus 로고
    • For a preliminary communication see
    • For a preliminary communication see: Fleming, F. F.; Gudipati, S. Org. Lett. 2006, 8, 1557.
    • (2006) Org. Lett , vol.8 , pp. 1557
    • Fleming, F.F.1    Gudipati, S.2
  • 41
    • 37049085893 scopus 로고    scopus 로고
    • Several cleverly designed conjugate additions to enones have trapped the presumed intermediates by employing internal radical traps. The yields of trapped product are typically in the range of 5-10% and in some cases the radical is unable to be intercepted: (a) Sarandeses, L. A, Mourino, A, Luche, J.-L. J. Chem. Soc, Chem. Commun. 1992, 798
    • Several cleverly designed conjugate additions to enones have trapped the presumed intermediates by employing internal radical traps. The yields of trapped product are typically in the range of 5-10% and in some cases the radical is unable to be intercepted: (a) Sarandeses, L. A.; Mourino, A.; Luche, J.-L. J. Chem. Soc, Chem. Commun. 1992, 798.
  • 44
    • 24044470646 scopus 로고    scopus 로고
    • For a general overview see: a
    • For a general overview see: (a) Li, C.-J. Chem. Rev. 2005, 105, 3095.
    • (2005) Chem. Rev , vol.105 , pp. 3095
    • Li, C.-J.1
  • 45
    • 34548719919 scopus 로고    scopus 로고
    • Li, C.-J.; Chan, T.-H. Metal-Mediated Reactions. In Organic Reactions in Aqueous Media; Wiley-Interscience: New York, 1997; Chapter 4.
    • (b) "Li, C.-J.; Chan, T.-H. Metal-Mediated Reactions. In Organic Reactions in Aqueous Media; Wiley-Interscience: New York, 1997; Chapter 4.
  • 47
    • 0001500051 scopus 로고    scopus 로고
    • Ultrasonic irradition was deleterious in contrast to reactions with less highly substituted enones: Luche, J. L.; Allavena, C.; Petrier, C.; Dupuy, C. Tetrahedron Lett. 1988, 29, 5373.
    • Ultrasonic irradition was deleterious in contrast to reactions with less highly substituted enones: Luche, J. L.; Allavena, C.; Petrier, C.; Dupuy, C. Tetrahedron Lett. 1988, 29, 5373.
  • 51
    • 34548718812 scopus 로고    scopus 로고
    • Lewis Acid Catalysis in Clean Solvents, Water, and Supercritical Carbon Dioxide Clean Solvents: Alternative Media for Chemical Reactions and Processing; ACS Symp. Ser.; American Chemical Society: Washington, DC, 2002; No. 819, pp 151-165.
    • (b) "Lewis Acid Catalysis in Clean Solvents, Water, and Supercritical Carbon Dioxide" Clean Solvents: Alternative Media for Chemical Reactions and Processing; ACS Symp. Ser.; American Chemical Society: Washington, DC, 2002; No. 819, pp 151-165.
  • 53
    • 0000720837 scopus 로고    scopus 로고
    • Blanchard, P.; Da Silva, A. D.; El, Kortbi, M. S.; Fourrey, J.-L.; Machado, A. S.; Robert-Gero, M. J. Org. Chem. 1993, 58, 6517.
    • (b) Blanchard, P.; Da Silva, A. D.; El, Kortbi, M. S.; Fourrey, J.-L.; Machado, A. S.; Robert-Gero, M. J. Org. Chem. 1993, 58, 6517.
  • 56
    • 23644440971 scopus 로고    scopus 로고
    • The related addition to ethyl vinyl sulfone affords a 2:1 ratio of cyclopentylmethyl and hexenyl addition: Zhao, M. M.; Qu, C.; Lynch, J. E. J. Org. Chem. 2005, 70, 6944.
    • The related addition to ethyl vinyl sulfone affords a 2:1 ratio of cyclopentylmethyl and hexenyl addition: Zhao, M. M.; Qu, C.; Lynch, J. E. J. Org. Chem. 2005, 70, 6944.
  • 57
    • 34548731391 scopus 로고    scopus 로고
    • Related radical probes with enones and enoates similarly imply radicaloid intermediates and in one instance intramolecular cyclization onto a pendant alkyne occurs in 10% yield.18
    • 18
  • 59
    • 0000720837 scopus 로고    scopus 로고
    • Blanchard, P.; Da Silva, A. D.; El, Kortbi, M. S.; Fourrey, J.-L.; Machado, A. S.; Robert-Gero, M. J. Org. Chem. 1993, 58, 6517.
    • Blanchard, P.; Da Silva, A. D.; El, Kortbi, M. S.; Fourrey, J.-L.; Machado, A. S.; Robert-Gero, M. J. Org. Chem. 1993, 58, 6517.
  • 62
    • 34548722197 scopus 로고    scopus 로고
    • After the reaction the octagonal stir bar is noticeably concave as a result of the abrasive action of silica on the Teflon coating
    • After the reaction the octagonal stir bar is noticeably concave as a result of the abrasive action of silica on the Teflon coating.
  • 69
    • 34548796588 scopus 로고    scopus 로고
    • Unpublished X-ray analysis of the material indicated that the material is not a copper hydride: ref 18, footnote 7.
    • Unpublished X-ray analysis of the material indicated that the material is not a copper hydride: ref 18, footnote 7.
  • 73
    • 34548805960 scopus 로고    scopus 로고
    • 2 reference code 01-089-0138; zinc metal reference code 01-087-0713, CuI reference code 01-083-1107.
    • 2 reference code 01-089-0138; zinc metal reference code 01-087-0713, CuI reference code 01-083-1107.
  • 74
    • 34548759153 scopus 로고    scopus 로고
    • The Cu(K) peak appears because the sample is adhered to a double-sided conductive carbon tape
    • The Cu(K) peak appears because the sample is adhered to a double-sided conductive carbon tape.
  • 75
    • 34548725650 scopus 로고    scopus 로고
    • 3Zn reference code 03-065-6567.
    • 3Zn reference code 03-065-6567.
  • 76
    • 34548717109 scopus 로고    scopus 로고
    • Transmission electron miscroscopy coupled with EDS failed to locate individual copper particles
    • Transmission electron miscroscopy coupled with EDS failed to locate individual copper particles.
  • 79
    • 85010592651 scopus 로고    scopus 로고
    • For a related cyclization to an angular nitrile-containing cis-hydrindane see: Sato, M.; Suzuki, T.; Morisawa, H.; Fujita, S.; Inukai, N.; Kaneko, C. Chem. Pharm. Bull. 1987, 35, 3647. The cis-hydrindane stereochemistry was secured by hydrolysis to the corresponding amide and spectral correlation with a previously characterized sample: Molander, G. A.; Dowdy, E. D.; Schumann, H. J. Org. Chem. 1998, 63, 3386.
    • For a related cyclization to an angular nitrile-containing cis-hydrindane see: Sato, M.; Suzuki, T.; Morisawa, H.; Fujita, S.; Inukai, N.; Kaneko, C. Chem. Pharm. Bull. 1987, 35, 3647. The cis-hydrindane stereochemistry was secured by hydrolysis to the corresponding amide and spectral correlation with a previously characterized sample: Molander, G. A.; Dowdy, E. D.; Schumann, H. J. Org. Chem. 1998, 63, 3386.
  • 81
    • 34548736052 scopus 로고    scopus 로고
    • -1: Eliel, E. L.; Wilen, S. H.; Mander, L. N. in Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 696-7.
    • -1: Eliel, E. L.; Wilen, S. H.; Mander, L. N. in Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 696-7.
  • 82
    • 34548802495 scopus 로고    scopus 로고
    • 1H NMR analysis of the crude reaction mixture failed to identify any of the diastereomeric cis-decalin.
    • 1H NMR analysis of the crude reaction mixture failed to identify any of the diastereomeric cis-decalin.
  • 83
    • 34548712441 scopus 로고    scopus 로고
    • b (a) Spanenburg, W. J.; Snell, B. E.; Su, M.-C. Microchem. J. 1993, 47, 79.
    • b (a) Spanenburg, W. J.; Snell, B. E.; Su, M.-C. Microchem. J. 1993, 47, 79.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.