Conclusions
The observation of diastereotopism of the methoxy groups (at a distance of eight bonds from the asymmetric center) in the PMR spectra of 4,4-disubstituted l-(dimethylphosphorylmethylidene)-2,5-cyclohexadienes has been used to demonstrate the chirality of para-semiquinoid systems containing a heteroatom in the unsaturated exo-fragment of the molecule and two substituents distinguishable from each other in the geminal position.
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O. A. Reutov, V. A. Nikanorov, and V. I. Rozenberg, in: The Tenth International Conference on Organometallic Chemistry, Abstracts, Toronto (1981), p. 35.
V. I. Rozenberg, V. A. Nikanorov, G. V. Gavrilova, B. I. Ginsburg, and O. A. Reutov, Izv. Akad. Nauk SSSR, Ser. Khim., 2182 (1982).
K. Mislow and M. Raban, in: Selected Problems in Stereochemistry [Russian translation], Mir, Moscow (1970), p. 9; Top. Stereochem., I, 1 (1967).
V. I. Rozenberg, V. A. Nikanarov, B. I. Ginzburg, and O. A. Reutov, Izv. Akad. Nauk SSSR, Ser. Khim., 1213 (1983).
M. I. Kabachnik, T. A. Mastryukova, É. I. Fedin, A. É. Shipov, M. S. Vaisberg, P. V. Petrovskii, and L. L. Morozov, Izv. Akad. Nauk SSSR, Ser. Khim., 613 (1975).
N. S. Bhacca and D. H. Williams, Tetrahedron Lett., 3127 (1964).
J. E. Anderson, Tetrahedron Lett., 4713 (1965).
H. D. Beckhaus, J. Schaetzer, and C. Rüchardt, Tetrahedron Lett., 3307 (1983).
G. P. Schiemenz and H. P. Hansen, Angew. Chem. Int. Ed. Engl.,12, 400 (1973); G. P. Schiemenz, J. Pistor, and M. Wolf, Chem. Scr.,18, 67 (1981).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2296–2299, October, 1986.
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Nikanorov, V.A., Glnzburg, B.I., Bakhmutov, V.I. et al. Chirality of exo-heterosubstituted semiquinoid systems. Russ Chem Bull 35, 2099–2102 (1986). https://doi.org/10.1007/BF00957532
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DOI: https://doi.org/10.1007/BF00957532