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Synthesis and selective hydrogenation of dibenzylbenzenes and α,α′-bis(benzylphenyl)xylenes

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Summary

  1. 1.

    The following previously undescribed hydrocarbons were prepared: 2-(cyclohexylmethyl)biphenyl, 3-(cyclohexylmethyl)biphenyl, 4-(cyclohexylmethyl)biphenyl, p-biscyclohexylmethylbenzene, 2-(cyclohexylmethyl)bicyclohexyl, 3-(cyclohexylmethyl)bicyclohexyl, 4-(cyclohexylmethyl)bicyclohexyl, 1,2-biscyclohexylmethylcyclohexane, 1,4-biscyclohexylmethylcyclohexane,α,α′-bis-o-benzylphenylxylene, and 1,4-bis[[4-(cyclohexylmethyl)cyclohexyljmethyl] cyclohexane.

  2. 2.

    The hydrogenation of dibenzylbenzenes andα,α′-bisbenzylphenylxylenes of various structure goes in various ways. Thus, under identical conditions of hydrogenation over PtO2 in 2-, 3-, and 4-benzylbiphenyls only one ring is hydrogenated, in p-dibenzylbenzene two rings are hydrogenated, and in α,α′-bis-p-benzylphenyl-p-xylene all five rings are hydrogenated. The selective hydrogenation ofα,α′-bis-p-benzylphenyl-p-xylene could not be effected, either over PtO2 or over Raney nickel.

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Literature cited

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 124–133, January, 1965

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Chel'tsova, M.A., Petrov, A.D., Lubuzh, E.D. et al. Synthesis and selective hydrogenation of dibenzylbenzenes and α,α′-bis(benzylphenyl)xylenes. Russ Chem Bull 14, 107–115 (1965). https://doi.org/10.1007/BF00854870

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Keywords

  • Hydrogenation
  • Nickel
  • Hydrocarbon
  • Cyclohexane
  • Xylene