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Original Articles

REGIOCHEMICAL STEERING AND ASSIGNMENT IN CYCLOADDITIONS OF NITRONES TO DIPHENYLVINYLPHOSPHINE OXIDE

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Pages 135-138 | Received 07 Jul 1988, Published online: 23 Oct 2006

References

  • Present address: Universita' della Basilicata, Istituto di Chimica, Via N. Sauro 85, 85100 Potenza, Italy
  • Black , St. D. C. , Crozier , R. F. and Davies , V. C. 1975 . Synthesis , : 205
  • Tufariello , J. J. 1984 . 1,3-Dipolar Cycloaddition Chemistry , Edited by: Padwa , A. vol. 2 , 83 New York : Wiley-Interscience .
  • Arbuzov , B. A. , Lisin , A. F. and Dianova , E. N. 1980 . Izv. Akad. Nauk SSSR, Ser. Khim. , : 207 See also
  • Koizumi , T. , Hirai , H. and Yoshii , E. 1982 . J. Org. Chem. , 47 : 4004
  • Kolokoltseva , I. G. , Chistokletov , V. N. , Ionin , B. I. and Petrov , A. A. 1968 . Zh. Obshch. Khim. , 38 : 1248 1203 Engl. Edition
  • Zbiral , E. 1974 . Synthesis , : 775 This work has been later reviewed
  • Arbuzov , B. A. , Lisin , A. F. and Dianova , E. N. 1980 . Izv. Akad. Nauk SSSR. Ser. Khim. , : 715 For studies related to a phosphonyl group see
  • Arbuzov , B. A. , Samitov , Yu. Yu. , Dianova , E. N. and Lisin , A. F. 1976 . Izv. Akad. Nauk SSSR. Ser. Khim. , : 2779
  • Arbuzov , B. A. , Samitov , Yu. Yu. , Dianova , E. N. and Lisin , A. F. 1975 . Izv. Akad. Nauk SSSR. Ser. Khim. , : 2559 See also ref. 11
  • Brandi , A. , Cannavo , P. , Pietrusiewicz , K. M. , Zablocka , M. , Wieczorek , M. and Bujacz , G. manuscript in preparation
  • IP value (7.75 eV)8 for C,N-diphenylnitrone implies that its HOMO lies somewhat higher than the HOMO of the corresponding C-phenyl-N-methylnitrone (IP = 8.01 eV)8; this difference might account for the observed shift in regioselectivity
  • Armen , G. H. , Braunstein , C. , Weinstein , M. I. and Baker , A. D. 1979 . Tetrahedron Lett. , : 4197
  • The replacement of Ph—P by Me—P substituent in the phosphine oxide results in similar reversal of the preferred regiochemistry. Cf. ref. 6.
  • Due to complexity of the 1H NMR spectra caused by extensive proton-phosphorus coupling the stereochemical assignment should be regarded tentative. The observed formation of only one of the two possible 4-substituted stereoisomers in each studied case is most likely to originate from the preference for a transition state in which phosphinyl group and nitrone C-substituent are oriented away from each other to avoid unfavourable interactions
  • Arbuzov , B. A. , Samitov , Yu. Yu. , Dianova , E. N. and Lisin , A. F. 1975 . Izu. Akad. Nauk SSSR, Ser. Khim. , : 909 For a relevant reinvestigation see

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