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Volumn 59, Issue 43, 2003, Pages 8543-8550

Free-radical functionalisation of vinylcyclopropanes

Author keywords

Allylsilanes; Annulation; Cyclopropanes; Radicals; Selenium and compounds; Silicon and compounds

Indexed keywords

2 SILYLBICYCLO[3.1.0]HEXANE; ALKANE DERIVATIVE; ALKENE DERIVATIVE; CYCLOPENTENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; ETHYL[5 (DIMETHYLPHENYLSILYL) 4 (PHENYLTHIO)CYCLOPENT 2 EN 1 YL]ACETATE; ETHYL[5 (DIMETHYLPHENYLSILYL) 4 [(4 METHYLPHENYL)SULFONYL]CYCLOPENT 2 EN 1 YL](PHENYLSELENYL)ACETATE; FREE RADICAL; FUNCTIONAL GROUP; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 0141817913     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.013     Document Type: Article
Times cited : (18)

References (33)
  • 3
    • 0000149724 scopus 로고    scopus 로고
    • (c) Landais Y. Chimia. 52:1998;104-111.
    • (1998) Chimia , vol.52 , pp. 104-111
    • Landais, Y.1
  • 14
    • 85031051878 scopus 로고    scopus 로고
    • 3B (0.2 equiv.) at 60°C, instead of PhSH led to recovered starting material
    • 3B (0.2 equiv.) at 60°C, instead of PhSH led to recovered starting material.
  • 17
    • 0035936776 scopus 로고    scopus 로고
    • E/Z configuration of 8 was assigned based on the deshielding of protons in γ-position by the ester function. For instance, CHSi was found at 3.97 ppm in isomer-Z and 2.86 ppm in isomer-E. Conversely, the γ-vinylic H was found at 6.36 ppm in isomer Z and 7.39 ppm in isomer-E. This is in good agreement with a recent report on magnetic anisotropy of an ester group in related analogs, see: Toochinda M.T., Bartlett P.A. J. Org. Chem. 66:2001;1326-1333.
    • (2001) J. Org. Chem. , vol.66 , pp. 1326-1333
    • Toochinda, M.T.1    Bartlett, P.A.2
  • 18
    • 0000011388 scopus 로고
    • -1 (25°C): (a) Wagner P.J., Sedon J.H., Lindstrom M.J. J. Am. Chem. Soc. 100:1978;2579-2580. and references cited therein. See also: (b) Chatgilialoglu C., Altieri A., Fischer H. J. Am. Chem. Soc. 124:2002;12816-12823 (c) Timokhin V.I., Gastaldi S., Bertrand M.P., Chatgilialoglu C. J. Org. Chem. 68:2003;3532-3537.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 2579-2580
    • Wagner, P.J.1    Sedon, J.H.2    Lindstrom, M.J.3
  • 19
    • 0037202139 scopus 로고    scopus 로고
    • -1 (25°C): (a) Wagner P.J., Sedon J.H., Lindstrom M.J. J. Am. Chem. Soc. 100:1978;2579-2580. and references cited therein. See also: (b) Chatgilialoglu C., Altieri A., Fischer H. J. Am. Chem. Soc. 124:2002;12816-12823 (c) Timokhin V.I., Gastaldi S., Bertrand M.P., Chatgilialoglu C. J. Org. Chem. 68:2003;3532-3537.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12816-12823
    • Chatgilialoglu, C.1    Altieri, A.2    Fischer, H.3
  • 20
    • 0037414540 scopus 로고    scopus 로고
    • -1 (25°C): (a). and references cited therein. See also: (b)
    • -1 (25°C): (a) Wagner P.J., Sedon J.H., Lindstrom M.J. J. Am. Chem. Soc. 100:1978;2579-2580. and references cited therein. See also: (b) Chatgilialoglu C., Altieri A., Fischer H. J. Am. Chem. Soc. 124:2002;12816-12823 (c) Timokhin V.I., Gastaldi S., Bertrand M.P., Chatgilialoglu C. J. Org. Chem. 68:2003;3532-3537.
    • (2003) J. Org. Chem. , vol.68 , pp. 3532-3537
    • Timokhin, V.I.1    Gastaldi, S.2    Bertrand, M.P.3    Chatgilialoglu, C.4
  • 22
    • 85031054285 scopus 로고    scopus 로고
    • 5 showed that the intermolecular trapping of related alkenes was, as expected, not stereoselective, but that the 5-exo-trig cyclisation proceeded with good stereocontrol leading to the cis-ring junction
    • 5 showed that the intermolecular trapping of related alkenes was, as expected, not stereoselective, but that the 5-exo-trig cyclisation proceeded with good stereocontrol leading to the cis-ring junction.
  • 24
    • 0024803227 scopus 로고
    • The intermolecular radical allylation using allylsulfones and ditin derivatives has been reported: Keck G.E., Tafesh A.M. J. Org. Chem. 54:1989;5845-5846. For other related chain reactions involving sulfonyl radicals and ditin derivatives, see: Ollivier C., Renaud P. J. Am. Chem. Soc. 123:2001;4717-4727. and references cited therein.
    • (1989) J. Org. Chem. , vol.54 , pp. 5845-5846
    • Keck, G.E.1    Tafesh, A.M.2
  • 25
    • 0034827901 scopus 로고    scopus 로고
    • The intermolecular radical allylation using allylsulfones and ditin derivatives has been reported: For other related chain reactions involving sulfonyl radicals and ditin derivatives, see: and references cited therein
    • The intermolecular radical allylation using allylsulfones and ditin derivatives has been reported: Keck G.E., Tafesh A.M. J. Org. Chem. 54:1989;5845-5846. For other related chain reactions involving sulfonyl radicals and ditin derivatives, see: Ollivier C., Renaud P. J. Am. Chem. Soc. 123:2001;4717-4727. and references cited therein.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4717-4727
    • Ollivier, C.1    Renaud, P.2
  • 30
    • 85031061464 scopus 로고    scopus 로고
    • 1H NMR analysis
    • 1H NMR analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.