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Volumn 54, Issue 28, 1998, Pages 8207-8216

Attempts at vinyl radical carbonylation through cyclization onto carbonyl and cyano groups

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; NITRILE; VINYL DERIVATIVE;

EID: 0032500149     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00458-X     Document Type: Article
Times cited : (21)

References (34)
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    • (1991) Comprehensive Organic Synthesis , vol.4
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    • 5. Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc., 1991, 113, 5791; Beckwith, A, L. J.; Hay, B. P. J. Am. Chem. Soc., 1989, 111, 2674.
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    • Walton, R.1    Fraser-Reid, B.2
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    • 5. Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc., 1991, 113, 5791; Beckwith, A, L. J.; Hay, B. P. J. Am. Chem. Soc., 1989, 111, 2674.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2674
    • Beckwith, A.L.J.1    Hay, B.P.2
  • 17
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    • 7. Kim, S.; Yoon, S. Y. J. Chem. Soc., Chem. Commun., 1996, 1335; Dowd, P.; Wilk, B. K. J. Am. Chem. Soc., 1992. 114, 7949.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7949
    • Dowd, P.1    Wilk, B.K.2
  • 24
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    • Fluorobenzene is a convenient solvent for radical reactions, owing to its low toxicity
    • 11. Fluorobenzene is a convenient solvent for radical reactions, owing to its low toxicity.
  • 25
    • 85038530291 scopus 로고    scopus 로고
    • On the other hand, we have recently evidenced (see ref. 10d) that the cyclization rate of vinyl radicals is not largely dependent on the resonance stabilization of radical adducts
    • 12. On the other hand, we have recently evidenced (see ref. 10d) that the cyclization rate of vinyl radicals is not largely dependent on the resonance stabilization of radical adducts.
  • 26
    • 85038537331 scopus 로고    scopus 로고
    • 1H NMR data, which show the atropisomers to be still present at 100 °C
    • 1H NMR data, which show the atropisomers to be still present at 100 °C.
  • 27
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    • However, in a repeated chromatography or on standing at the air no further oxidation of 41 was observed
    • 14. However, in a repeated chromatography or on standing at the air no further oxidation of 41 was observed.
  • 29
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    • 15. For vinyl sulfides oxidation see: Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P. Tetrahedron Lett., 1993, 34, 3595; Capella, L.; Montevecchi, P. C ; Nanni, D. J. Org. Chem., 1994, 59, 7379.
    • (1994) J. Org. Chem. , vol.59 , pp. 7379
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    • Radical addition involving CC triple bonds
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    • 16. Chatgilialoglu, C.; Ferreri, C. "Radical Addition involving CC Triple Bonds" in The Chemistry of Triple-bonded Functional Groups, Patai, S., Ed.; J. Wiley: New York, 1994; Suppl. C2, Vol. 2, Chapter 16
    • (1994) The Chemistry of Triple-bonded Functional Groups , vol.2 , Issue.SUPPL. C2
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  • 31
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    • Similarly, in a independent experiment we observed that no addition products were formed from phenyl(trimethylsilyl)acetylene and benzenethiol under the reaction conditions employed. In contrast, reaction of benzenethiol with aryl(trimethylsilyl)acetylene having a fairly good radical acceptor in 2-position, such as an azido function, smoothly lead to cyclization products. (These results will be published elsewhere)
    • 17. Similarly, in a independent experiment we observed that no addition products were formed from phenyl(trimethylsilyl)acetylene and benzenethiol under the reaction conditions employed. In contrast, reaction of benzenethiol with aryl(trimethylsilyl)acetylene having a fairly good radical acceptor in 2-position, such as an azido function, smoothly lead to cyclization products. (These results will be published elsewhere).


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