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Volumn 509, Issue 1, 1996, Pages 1-8

Synthesis of asymmetrical aryl-tin compounds by cleavage of alkyl-tin bonds with sodium metal in liquid ammonia followed by SRN1 reactions with chloroarenes

Author keywords

Electron transfer; Nucleophilic substitution; Srn1; Tin

Indexed keywords


EID: 0002969283     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(95)05800-5     Document Type: Article
Times cited : (13)

References (28)
  • 10
    • 85030025478 scopus 로고    scopus 로고
    • note
    • RN1 pattern. When the substrate is an iodoarene, an halogen metal exchange mechanism operates, leading to the reduced product (the arene) instead of the substitution product, since the intermediate anion is immediately protonated by ammonia [9].
  • 11
    • 85030013641 scopus 로고
    • S. Patai and Z. Rappoport (eds.) Wiley, Chichester, UK, Chapter 16
    • RN1 Mechanism, ACS Monograph 178, American Chemical Society, Washington, DC, 1983; (c) R.K. Norris, in B.M. Trost (ed.), Comprehensive Organic Synthesis, Vol. IV, Pergamon, p. 451.
    • (1983) The Chemistry of Functional Groups , Issue.SUPPL. D
    • Norris, R.K.1
  • 12
    • 0003780317 scopus 로고
    • ACS Monograph 178, American Chemical Society, Washington, DC
    • RN1 Mechanism, ACS Monograph 178, American Chemical Society, Washington, DC, 1983; (c) R.K. Norris, in B.M. Trost (ed.), Comprehensive Organic Synthesis, Vol. IV, Pergamon, p. 451.
    • (1983) RN1 Mechanism
    • Rossi, R.A.1    De Rossi, R.H.2
  • 13
    • 0000866608 scopus 로고    scopus 로고
    • B.M. Trost (ed.), Pergamon
    • RN1 Mechanism, ACS Monograph 178, American Chemical Society, Washington, DC, 1983; (c) R.K. Norris, in B.M. Trost (ed.), Comprehensive Organic Synthesis, Vol. IV, Pergamon, p. 451.
    • Comprehensive Organic Synthesis , vol.4 , pp. 451
    • Norris, R.K.1
  • 14
    • 0343093830 scopus 로고
    • P.G. Harrison (ed.), Blackie, London
    • P.G. Harrison, in P.G. Harrison (ed.), Chemistry of Tin, Blackie, London, 1989, p. 13.
    • (1989) Chemistry of Tin , pp. 13
    • Harrison, P.G.1
  • 16
    • 84981769090 scopus 로고
    • In 1979, Weichmann and Tzschach (Z. Anorg. Allg. Chem., 458 (1979) 291) reported the reaction between phenyltricyclohexyltin and potassium in liquid ammonia, which afforded dicyclohexylphenyltin anion, contrary to their expectation. This reaction was not investigated further.
    • (1979) Z. Anorg. Allg. Chem. , vol.458 , pp. 291
    • Weichmann1    Tzschach2
  • 23
    • 85030021348 scopus 로고    scopus 로고
    • note
    • The equipment used for reactions in liquid ammonia is described in detail in the Appendix of Ref. [11b).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.