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Volumn 63, Issue 48, 2007, Pages 11959-11964

Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to C{double bond, long}N double bonds

Author keywords

Alkyl phenyl telluride; Diethylzinc; Dimethylzinc; Radical addition to imino group

Indexed keywords

CARBON; IODIDE; NITROGEN; ORGANOTELLURIUM DERIVATIVE; PHENYLORGANOTELLURIUM; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

EID: 35349003378     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.014     Document Type: Article
Times cited : (25)

References (62)
  • 16
    • 33745026453 scopus 로고    scopus 로고
    • For a general review on dialkylzincs in radical chemistry, see:
    • For a general review on dialkylzincs in radical chemistry, see:. Bazin S., Feray L., and Bertrand M.P. Chimia 60 (2006) 260
    • (2006) Chimia , vol.60 , pp. 260
    • Bazin, S.1    Feray, L.2    Bertrand, M.P.3
  • 17
    • 35348947753 scopus 로고    scopus 로고
    • For reviews on radical addition to C{double bond, long}N bonds, see:
  • 20
    • 33751525766 scopus 로고    scopus 로고
    • Dimethylzinc was also shown to be a convenient source of methyl radical in conjugate radical addition, see:
    • Dimethylzinc was also shown to be a convenient source of methyl radical in conjugate radical addition, see:. Bazin S., Feray L., Vanthuyne N., Siri D., and Bertrand M.P. Tetrahedron 63 (2007) 77
    • (2007) Tetrahedron , vol.63 , pp. 77
    • Bazin, S.1    Feray, L.2    Vanthuyne, N.3    Siri, D.4    Bertrand, M.P.5
  • 21
    • 4544253643 scopus 로고    scopus 로고
    • For a review on radical reactions involving organotellurium compounds, see:
    • For a review on radical reactions involving organotellurium compounds, see:. Yamago S. Synlett (2004) 1875
    • (2004) Synlett , pp. 1875
    • Yamago, S.1
  • 22
    • 12944280242 scopus 로고    scopus 로고
    • For a more general review on organotelluriums chemistry, see:
    • For a more general review on organotelluriums chemistry, see:. Petragnani N., and Stefani H.A. Tetrahedron 61 (2005) 1613
    • (2005) Tetrahedron , vol.61 , pp. 1613
    • Petragnani, N.1    Stefani, H.A.2
  • 24
    • 35348957663 scopus 로고    scopus 로고
    • For representative examples, see:
  • 41
    • 0031562033 scopus 로고    scopus 로고
    • 1H NMR spectrum of the reaction mixture after filtration on a short pad of silica gel showed that EtTePh was formed in a 35:65 ratio with respect to 2d. Unexpectedly, the ratio increased in degassed solution. It reached 45:55. When i-PrTePh (2a) was submitted to the same conditions, the formation of EtTePh was also dependent on the presence of oxygen, but the EtTePh:i-PrTePh ratio was 4:96 in degassed solution, and 25:75 in the presence of air. In the latter case, the Zn/Te exchange is in agreement with an oxygen-promoted radical mechanism.
    • 2 was shown to catalyze tellurium-zinc exchange reactions. Both alkyl and phenyl groups could be transferred to zinc, see:. Stüdemann T., Gupta V., Engman L., and Knochel P. Tetrahedron Lett. 38 (1997) 1005
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1005
    • Stüdemann, T.1    Gupta, V.2    Engman, L.3    Knochel, P.4
  • 42
    • 35348944263 scopus 로고    scopus 로고
    • 2-catalyzed addition of diethylzinc to tosylimines, see:
  • 45
    • 35348964964 scopus 로고    scopus 로고
    • note
    • In situ reduction of Cu(II) and addition of an alkylcopper cannot be ruled out under these conditions.
  • 46
    • 35349030093 scopus 로고    scopus 로고
    • note
    • 1H NMR of the crude product for ethyl radical adduct (11b) that was formed in small amount.
  • 57
    • 0002963299 scopus 로고    scopus 로고
    • 3, 2H), 3.40 (sext, 1H, J=7.0), 7.22-7.37 (m, 3H), 7.82-7.85 (d, 2H, J=8.1)
    • 3, 2H), 3.40 (sext, 1H, J=7.0), 7.22-7.37 (m, 3H), 7.82-7.85 (d, 2H, J=8.1)
    • (1996) Chem. Commun. , pp. 1419
    • Schiesser, C.H.1    Skidmore, M.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.