메뉴 건너뛰기




Volumn 134, Issue 47, 2012, Pages 19358-19361

Nucleophilic substitution reaction at the nitrogen of arylsulfonamides with phosphide anion

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOPHILIC SUBSTITUTION REACTIONS; PHOSPHIDE ANIONS;

EID: 84870368766     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja309642r     Document Type: Article
Times cited : (41)

References (39)
  • 13
    • 49549169249 scopus 로고
    • High azaphilicity of phosphorus has been revealed by a substitution reaction of O -(2,4-dinitrophenyl)hydroxylamine; see: Oae, S.; Yamamoto, F. Tetrahedron Lett. 1973, 14, 5143
    • (1973) Tetrahedron Lett. , vol.14 , pp. 5143
    • Oae, S.1    Yamamoto, F.2
  • 14
    • 31544461484 scopus 로고    scopus 로고
    • The synthesis and applications of phosphines
    • For protection of P(III) by sulfur, see: In; Murphy, P. J. Oxford University Press: Oxford
    • For protection of P(III) by sulfur, see: Clarke, M. L.; Williams, J. M. J. The synthesis and applications of phosphines. In Organophosphorus Reagents; Murphy, P. J., Ed.; Oxford University Press: Oxford, 2004; p 26.
    • (2004) Organophosphorus Reagents , pp. 26
    • Clarke, M.L.1    Williams, J.M.J.2
  • 15
    • 84981816173 scopus 로고
    • It has been reported that the reaction of benzaldehyde tosylhydrazone and sodium phosphite affords the N -benzylidenehydrazide of phosphoric acid diethyl ester; see: Marek, T.; Janusz, R. Zeitschrift für Chemie 1990, 30, 246
    • (1990) Zeitschrift für Chemie , vol.30 , pp. 246
    • Marek, T.1    Janusz, R.2
  • 16
    • 0000751744 scopus 로고
    • It has been reported that the phosphide anion acts as an electron donor to alkyl halides and causes a radical-mediated substitution reaction; see: and references cited therein. Accordingly, we considered the possibility of a similar radical mechanism for the present reaction and performed mechanistic studies (vide infra)
    • It has been reported that the phosphide anion acts as an electron donor to alkyl halides and causes a radical-mediated substitution reaction; see: Ashby, E. C.; Gurumurthy, R.; Ridlehuber, R. W. J. Org. Chem. 1993, 58, 5832 and references cited therein. Accordingly, we considered the possibility of a similar radical mechanism for the present reaction and performed mechanistic studies (vide infra)
    • (1993) J. Org. Chem. , vol.58 , pp. 5832
    • Ashby, E.C.1    Gurumurthy, R.2    Ridlehuber, R.W.3
  • 19
    • 31544461484 scopus 로고    scopus 로고
    • The synthesis and applications of phosphines
    • Murphy, P. J. Oxford University Press: Oxford
    • Clarke, M. L.; Williams, J. M. J. The synthesis and applications of phosphines. In Organophosphorus Reagents; Murphy, P. J., Ed.; Oxford University Press: Oxford, 2004; pp 15-48. For a recent development in preparation of phosphide anion, see
    • (2004) Organophosphorus Reagents , pp. 15-48
    • Clarke, M.L.1    Williams, J.M.J.2
  • 29
    • 84922630623 scopus 로고    scopus 로고
    • Protection for the amino group
    • 4 th ed. John Wiley & Sons: New York
    • Wuts, P. G. M.; Greene, T. W. Protection for the amino group. In Protective Groups in Organic Synthesis, 4 th ed.; John Wiley & Sons: New York, 2006; pp 696-926.
    • (2006) Protective Groups in Organic Synthesis , pp. 696-926
    • Wuts, P.G.M.1    Greene, T.W.2
  • 35
    • 33748829250 scopus 로고    scopus 로고
    • Deprotection of tosylamides with silyllithium was reported by I. Fleming, et al., although they suggested that the reaction involved a nucleophilic attack to sulfur; see: Fleming, I.; Frackenpohl, J.; Ila, H. J. Chem. Soc., Perkin Trans. 1 1998, 1229
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 1229
    • Fleming, I.1    Frackenpohl, J.2    Ila, H.3
  • 36
    • 0027080836 scopus 로고
    • Ishizaki and Hoshino reported that the reaction of tosylamides and Red-Al in hot toluene afforded the corresponding amines. Although the reaction mechanism was not described in the literature, the reaction might proceed via a nucleophilic substitution reaction at nitrogen; see: Ishizaki, M.; Hoshino, O. J. Org. Chem. 1992, 57, 7285
    • (1992) J. Org. Chem. , vol.57 , pp. 7285
    • Ishizaki, M.1    Hoshino, O.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.