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Volumn , Issue 6, 2004, Pages 987-990

Radical chain reaction of benzenethiol with pentynylthiol esters: Production of aldehydes under stannane/silane-free conditions

Author keywords

Acyl radicals; Aldehydes; Benzenethiol; Reduction; Thiol esters

Indexed keywords

ALDEHYDE DERIVATIVE; RADICAL; SILANE DERIVATIVE; THIOESTER; THIOPHENOL;

EID: 3142711410     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822884     Document Type: Article
Times cited : (21)

References (37)
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    • For recent reviews on the chemistry of acyl radicals and their application in synthesis, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050. (b) Ryu, L; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (c) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
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    • For recent reviews on the chemistry of acyl radicals and their application in synthesis, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050. (b) Ryu, L; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (c) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
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    • For very recent productions of acyl radicals by oxidation of acyl hydrazine precursors see: (a) Braslau, R.; Anderson, M. O.; Rivera, F.; Jimenez, A.; Haddad, T.; Axon, J. R. Tetrahedron 2002, 58, 5513. (b) Bath, S.; Laso, N. M.; Lopez-Ruiz, H.; Quiclet-Sire, B.; Zard, S. Z. Chem. Commun. 2003, 204.
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    • For very recent examples of the use of selenoesters in acyl radical chemistry see: (a) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887. (b) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. Org. Lett. 2001, 3, 1697. (c) Bennasar, M.-L.; Roca, T.; Griera, R.; Bassa, M.; Bosch, J. J. Org. Chem. 2002, 67, 6268.
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    • note
    • 2), 69.50 (CH), 83.13 (C), 128.71 (CH), 129.07 (CH), 135.51 (C), 139.91 (C), 190.64 (CO).
  • 23
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    • note
    • 13C NMR spectral data, The vinyl sulfides 3a-h,j-m were generally obtained as an inseparable mixtures of the E- and Z-isomer.
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    • 2
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    • note
    • 9a
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    • note
    • The amount of the resulting vinyl sulfide adduct 3 was not significantly diminished when an alkanethiol such as methyl thioglycolate was used in place of benzenethiol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.