New chiral organophosphorus derivatizing agent for the determination of enantiomeric composition of chloro- and bromohydrins by 31P NMR spectroscopy

Tetrahedron Asymmetry

Volumn 11, Issue 6, 2000, Pages 1273-1278

  Reymond, Sébastien ^a   Brunel, Jean Michel ^a   Buono, Gérard ^a  

^a Ecole Centrale Marseille   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CHLORINE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL COMPOSITION; CHIRALITY; CRYSTAL STRUCTURE; DERIVATIZATION; ENANTIOMER; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0034615864     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00062-8     Document Type: Article

References (27)

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24. 1 from the systemic absences. A total of 1503 reflections were collected at T=298 K. The standards were measured after every 158 reflections. Selected bond distances (Å): P1-N3, 1.648(1); P1-N4, 1.691(1); P1-N20, 1.632(1); P1-B19, 1.912(1); N3-C7, 1.479(2); N3-C13, 1.471(2); N4-C6, 1.418(2). Selected bond angles (°): N3-P1-N4, 92.5(1); N3-P1-N20, 109.4(1); N4-P1-N20, 108.1(1); P1-N3-C7, 114.7(1); P1-N3-C13, 125.5(1); C7-N3-C13, 111.6(1); P1-N4-C12, 111.9(1); P1-N4-C6, 123.9(1); C6-N4-C12, 119.8(1); P1-N20-C22, 124.5(1); P1-N20-C21, 121.2(1). CCDC 139376.
25. It is noteworthy that when the reaction time is not long enough, traces of syn-4a and syn-4b diastereomers can be characterized. In this case, integration of the signals can still be correlated to the enantiomeric purity of the considered halohydrin.
26. S: 14.53 min (major).
27. Brunel, J. M.; Constantieux, T.; Buono, G. J. Org. Chem. 1999, 64, 8940.