Conclusions
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1.
The stereochemistry of heterogeneous and homogeneous hydrogenation of p-bornenylanisole is mainly determined by the accessibility of the double bonds of these compounds.
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2.
The reduction with p-norbornenylanisole by diimide leads to the formation of only the endoisomer whereas the reduction of p-norbornenylanisole by diimide fails because of steric factors involved.
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3.
The reduction of p-norbornenylanisole and p-bornenylanisole by sodium in liquid ammonia leads to the formation of only the appropriate endo-isomers. An interpretation of the stereochemical characteristics of this reaction has been advanced.
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Translated from Izvestiya Adademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2078–2082, September, 1970.
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Kheifits, L.A., Gol'dovskii, A.E., Kolomnikov, I.S. et al. Stereochemistry of heterogeneous and homogeneous hydrogenation of substituted bicyclo(2,2,1) heptenes. Russ Chem Bull 19, 1951–1954 (1970). https://doi.org/10.1007/BF00849779
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DOI: https://doi.org/10.1007/BF00849779