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Original Articles

SYNTHESIS, REACTIONS, AND STEREOCHEMICAL CORRELATIONS OF AN OPTICALLY ACTIVE TERVALELENT PHOSPHORUS THIO ESTER

, &
Pages 177-184 | Received 23 May 1986, Published online: 03 Jan 2007

References

  • Szafraniec , L. J. , Szafraniec , L. L. and Aaron , H. S. 1982 . J. Org. Chem. , 47 : 1936
  • Mikolajczyk , M. , Drabowicz , J. , Omelanczuk , J. and Fluck , E. 1975 . J. Chem. Soc., Chem. Commun. , : 382
  • Omelanczuk , J. and Mikolajczyk , M. 1976 . J. Chem. Soc., Chem. Commun. , : 1025 A (+ (-RR'P(SR(species also has been reported from a similar procedure by
  • Dimukhametov , M. N. and Nuretdinov , I. A. 1984 . Zhur. Obshch. Khim. , 54 : 1913
  • Szafraniec , L. J. , Reiff , L. P. and Aaron , H. S. 1970 . J. Amer. Chem. Soc. , 92 : 6391 The designation of the (S(-(—(-1 and (R(-(—(-2 configurations are corrections of the earlier assignments, due to results that were later reported by J. Donohue, N. Mandel, W. B. Farnham, R. K. Murray, K. Mislow, and H. P. Benschop, J. Amer. Chem. Soc., 93, 3792 (1971(
  • Akamsin , V. D. and Rizpolozhenskii , N. I. 1967 . Isvest. Akad, Nauk SSSR, Ser. Khim. , : 1987
  • Mikolajczyk , M. 1969 . J. Chem. Soc., Chem. Commun. , : 1221
  • Aaron , H. S. , Uyeda , R. T. , Frack , H. F. and Miller , J. I. 1962 . J. Amer. Chem. Soc. , 84 : 617
  • Cullis , P. M. 1984 . J. Chem. Soc., Chem. Commun. , : 1510
  • Denney , D. F. and Hanifin , J. W. 1963 . Tetrahedron Lett. , : 2177
  • Reiff , L. P. and Aaron , H. S. 1970 . J. Amer. Chem. Soc. , 92 : 5275
  • Omelanczuk , J. and Mikolajczyk , M. 1971 . Tetrahedron , 27 : 5587
  • In Scheme 1, the reagents are designated only for those reactions which are first reported at this time
  • The previously assigned9 value of [∝]D-24° (benzene(for 100% ee (—(-2 was based upon its conversion into (+(-Me(i-PrO(P(S(CI (7(, which had been erroneously assumed to have [∝]D-69.9° (CCI4(for 100% ee material. While the specific rotation for 7 was reported9 only for a chloroform solution, values of [∝]D + 66.0° (benzene(and [∝]D + 77.7° (neat, 1 dcm(also had been recorded (L. P. Reiff, unpublished data(. However, this sample was apparently only 78.5% ee, because 100% ee 7 has since been tentatively assigned as [∝]D + 98.9° (neat, 1 dcm).10

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