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Volumn 4, Issue 11, 2002, Pages 1835-1838

Stereochemical Study of Phosphonothioate Cleavage by a Metallomicelle

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL WARFARE AGENT; COPPER; METAL; THIOL DERIVATIVE;

EID: 0037198765     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0200394     Document Type: Article
Times cited : (15)

References (45)
  • 4
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    • Reviews: (a) Yang, Y.-C. Acc. Chem. Res. 1999, 32, 109. (b) Séguès, B.; Pérez, E.; Rico-Lattes, I.; Rivière, M.; Lattes, A. Bull. Soc. Chim. Fr. 1996, 133, 925 (c) Yang, Y.-C. Chem. Ind. (London) 1995, May 1, 334. (d) Yang, Y.-C.; Baker, J. A.; Ward, J. R. Chem. Rev. 1992, 92, 1729.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 109
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    • 18744380862 scopus 로고    scopus 로고
    • Reviews: (a) Yang, Y.-C. Acc. Chem. Res. 1999, 32, 109. (b) Séguès, B.; Pérez, E.; Rico-Lattes, I.; Rivière, M.; Lattes, A. Bull. Soc. Chim. Fr. 1996, 133, 925 (c) Yang, Y.-C. Chem. Ind. (London) 1995, May 1, 334. (d) Yang, Y.-C.; Baker, J. A.; Ward, J. R. Chem. Rev. 1992, 92, 1729.
    • (1996) Bull. Soc. Chim. Fr. , vol.133 , pp. 925
    • Séguès, B.1    Pérez, E.2    Rico-Lattes, I.3    Rivière, M.4    Lattes, A.5
  • 6
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    • May 1
    • Reviews: (a) Yang, Y.-C. Acc. Chem. Res. 1999, 32, 109. (b) Séguès, B.; Pérez, E.; Rico-Lattes, I.; Rivière, M.; Lattes, A. Bull. Soc. Chim. Fr. 1996, 133, 925 (c) Yang, Y.-C. Chem. Ind. (London) 1995, May 1, 334. (d) Yang, Y.-C.; Baker, J. A.; Ward, J. R. Chem. Rev. 1992, 92, 1729.
    • (1995) Chem. Ind. (London) , pp. 334
    • Yang, Y.-C.1
  • 7
    • 0001004984 scopus 로고
    • Reviews: (a) Yang, Y.-C. Acc. Chem. Res. 1999, 32, 109. (b) Séguès, B.; Pérez, E.; Rico-Lattes, I.; Rivière, M.; Lattes, A. Bull. Soc. Chim. Fr. 1996, 133, 925 (c) Yang, Y.-C. Chem. Ind. (London) 1995, May 1, 334. (d) Yang, Y.-C.; Baker, J. A.; Ward, J. R. Chem. Rev. 1992, 92, 1729.
    • (1992) Chem. Rev. , vol.92 , pp. 1729
    • Yang, Y.-C.1    Baker, J.A.2    Ward, J.R.3
  • 19
    • 0442266927 scopus 로고    scopus 로고
    • note
    • PNP = p-nitrophenyl; EPN = O-ethyl O-(4-nitrophenyl) phenyl-phosphonothioate.
  • 24
    • 0442268411 scopus 로고    scopus 로고
    • note
    • 9a
  • 25
    • 0442268413 scopus 로고    scopus 로고
    • note
    • 4a because of the simpler proton NMR spectrum of the former; the OMe resonance is ideal for tracking the stereochemistry (see below).
  • 28
    • 0442268415 scopus 로고    scopus 로고
    • Ph.D. Dissertation, Rutgers University, New Brunswick, NJ
    • Details appear in Morales-Rojas, H. Ph.D. Dissertation, Rutgers University, New Brunswick, NJ, 2001; pp 44-52, 65-68.
    • (2001) , pp. 44-52
    • Morales-Rojas, H.1
  • 29
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    • Hall, C. R.; Inch, T. D. Tetrahedron Lett. 1977, 18, 3761, 3765. Hall, C. R.; Inch, T. D. J. Chem. Soc., Perkin Trans. 1 1979, 1646
    • (1977) Tetrahedron Lett. , vol.18 , pp. 3761
    • Hall, C.R.1    Inch, T.D.2
  • 36
    • 0442265346 scopus 로고    scopus 로고
    • note
    • 1H NMR and satisfactory C, H, N microanalysis were obtained.
  • 37
    • 0442268416 scopus 로고    scopus 로고
    • note
    • 1H NMR and satisfactory C, H, N microanalysis were obtained.
  • 38
    • 0442266928 scopus 로고    scopus 로고
    • note
    • 3).
  • 41
    • 0442265348 scopus 로고    scopus 로고
    • note
    • P)-(-) correlations for 6.
  • 43
    • 0442263826 scopus 로고    scopus 로고
    • note
    • 3). The specific rotation of either pure enantiomer of 5 is ∼|44-46°|. However, a small but variable degree of racemization in the 9 → 5 conversion makes a precise value difficult to obtain.
  • 44
    • 0442268414 scopus 로고    scopus 로고
    • note
    • The uncertainty in enantiomeric composition reflects racemization in the methanolysis step of eq 2. which provides the Me-EPN; see above.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.