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Volumn 61, Issue 5, 1996, Pages 1689-1701

Sequence of reactant combination alters the course of the Staudinger reaction of azides with acyl derivatives. Bimanes. 30

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EID: 0001399558     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo950273q     Document Type: Article
Times cited : (54)

References (72)
  • 8
    • 49049124890 scopus 로고
    • Vaultier, M.; Knouzi, N.; Carrie, R. Tetrahedron Lett. 1983, 24, 763-764. Procedures using triethoxyphosphine (triethyl phosphite) for the conversion of alkyl azides to amines have been reported: Koziara. A.; Zwierzak. A. Synthesis 1992, 1063-1065.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 763-764
    • Vaultier, M.1    Knouzi, N.2    Carrie, R.3
  • 9
    • 0026475192 scopus 로고
    • Vaultier, M.; Knouzi, N.; Carrie, R. Tetrahedron Lett. 1983, 24, 763-764. Procedures using triethoxyphosphine (triethyl phosphite) for the conversion of alkyl azides to amines have been reported: Koziara. A.; Zwierzak. A. Synthesis 1992, 1063-1065.
    • (1992) Synthesis , pp. 1063-1065
    • Koziara, A.1    Zwierzak, A.2
  • 30
    • 85033867564 scopus 로고    scopus 로고
    • note
    • The nomenclature for the bimanes is explained in ref 25.
  • 33
    • 0040190445 scopus 로고
    • The reaction of N-alkyl- and N-aryliminophosphoranes and acyl halides has been shown to give C-chloro-, C-bromo-, and C-iodoimines via at least one "salt-like" intermediate Zbiral, E.; Bauer, E. Phosphorus 1972, 2, 35.
    • (1972) Phosphorus , vol.2 , pp. 35
    • Zbiral, E.1    Bauer, E.2
  • 38
    • 85033861032 scopus 로고    scopus 로고
    • note
    • The role of triazaphosphadiene as a synthetic intermediate (ref 34) in an intramolecular reaction with an imine is probably best explained by the authors' alternative mechanism, involving isomer ization through an adjacent double bond. The same applies to the reaction of triphenylphosphine with 2,3-diazido-1,4-naphthoquinone (ref 35). In both instances, reaction occurs at the middle nitrogen of the triazeno fragment.
  • 43
    • 85033868147 scopus 로고    scopus 로고
    • Unpublished results. Acyl thioesters, acylimidazoles, the adducts of carboxylic acids and earbodiimides, and acid anhydrides react with 2 or 3 to form acyl derivatives. Carboxylic acids, reported to react slowly in refluxing toluene (refs 43 and 44), are almost certainly reacting via the anhydride, since we found no reaction with 2 under our conditions
    • Shalev, D. E.; Radkowsky, A. E.; Kosower, E. M. Unpublished results. Acyl thioesters, acylimidazoles, the adducts of carboxylic acids and earbodiimides, and acid anhydrides react with 2 or 3 to form acyl derivatives. Carboxylic acids, reported to react slowly in refluxing toluene (refs 43 and 44), are almost certainly reacting via the anhydride, since we found no reaction with 2 under our conditions.
    • Shalev, D.E.1    Radkowsky, A.E.2    Kosower, E.M.3
  • 60
    • 0842318523 scopus 로고
    • The authors suggested a different mechanism in which the last step was an improbable O-to-N acyl transfer
    • D'Andrea, S. V.; Ghosh, A.; Wuyi, W.; Freeman, J. P.; Szmuczkovicz, J. J. Org. Chem. 1991, 56, 2680. The authors suggested a different mechanism in which the last step was an improbable O-to-N acyl transfer.
    • (1991) J. Org. Chem. , vol.56 , pp. 2680
    • D'Andrea, S.V.1    Ghosh, A.2    Wuyi, W.3    Freeman, J.P.4    Szmuczkovicz, J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.