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Chirality of exo-heterosubstituted semiquinoid systems

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

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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Literature cited

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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

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