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Volumn 39, Issue 40, 1998, Pages 7267-7270

Organosilane-mediated free radical cyclization reactions employing carbonyl traps

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBONYL DERIVATIVE; FREE RADICAL; HEXANOL; KETONE; PENTANOL; REAGENT; SILANE DERIVATIVE;

EID: 0032190813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01585-8     Document Type: Article
Times cited : (18)

References (35)
  • 12
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    • (b) ibid., 1987, 109, 6548-6549.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 6548-6549
  • 23
    • 1542554559 scopus 로고
    • H-O[M-H])}. See: (a) Seeman, J. I. Chem. Rev. 1983, 83, 83-134.
    • (1983) Chem. Rev. , vol.83 , pp. 83-134
    • Seeman, J.I.1
  • 25
    • 85038549109 scopus 로고    scopus 로고
    • note
    • 9. This situation will generally be the case in fast reversible cyclizations between an uncyclized carbon centred radical and a cyclized oxygen-centred radical. Thus, for the oxiranyl carbinyl radical system, control of the product ratios should be possible by judicious choice of H-atom donor.
  • 26
    • 4243749358 scopus 로고
    • 10. A number of organosilanes are useful radical reductants, see: (a) Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229-1251.
    • (1995) Chem. Rev. , vol.95 , pp. 1229-1251
    • Chatgilialoglu, C.1
  • 27
    • 0000829322 scopus 로고
    • and references cited therein
    • (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194, and references cited therein.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 188-194
    • Chatgilialoglu, C.1
  • 28
    • 0030590510 scopus 로고    scopus 로고
    • 11. Dimethyl 2,2′-azobisisobutyrate (DAB) was used as an initiator, having an almost identical half-life to AIBN See: Batey, R. A.; Pedram, B.; Yong, K.; Baquer, G. Tetrahedron Lett. 1996, 37, 6847-6850.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6847-6850
    • Batey, R.A.1    Pedram, B.2    Yong, K.3    Baquer, G.4
  • 30
    • 0030934055 scopus 로고    scopus 로고
    • (b) Jang, D. O. Synth. Commun. 1997, 27, 1023-1027. See also: Chatgilialoglu, C.; Ferreri, C.; Vecchi, D.; Lucarini, M.; Pedulli, G. F. J. Organomet. Chem. 1997, 546, 475-481.
    • (1997) Synth. Commun. , vol.27 , pp. 1023-1027
    • Jang, D.O.1
  • 33
    • 85038553286 scopus 로고    scopus 로고
    • note
    • 2 - EtOAc/hexanes) yielded 6a-e.
  • 34


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