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Hydrogenolysis of 7-phenyltricyclo[4.1.0.02,7]heptan-1-carboxylic acid. Synthesis of ketones with tricyclo[4.4.0.02,7]decane and tricyclo[5.4.0.02,8]undecane skeletons

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Abstract

Hydrogenation of 7-phenyltricyclo[4.1.0.02,7]heptane-1-carboxylic acid over Raney nickel occurred in the syn-stereoselective fashion to give anti-7-phenylbicyclo[3.1.1]heptane-exo-6-carboxylic acid. The latter was used to synthesize 4,5-benzotricyclo[4.4.0.02,7]dec-4-en-3-one and two isomeric higher homologs, 5,6-benzotricyclo[5.4.0.02,8]undec-5-en-3-and-4-ones.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    R. N. Zolotarev & V. V. Razin

Authors
  1. R. N. Zolotarev
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  2. V. V. Razin
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Correspondence to V. V. Razin.

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Original Russian Text © R.N. Zolotarev, V.V. Razin, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 8, pp. 1147–1151.

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Zolotarev, R.N., Razin, V.V. Hydrogenolysis of 7-phenyltricyclo[4.1.0.02,7]heptan-1-carboxylic acid. Synthesis of ketones with tricyclo[4.4.0.02,7]decane and tricyclo[5.4.0.02,8]undecane skeletons. Russ J Org Chem 43, 1139–1143 (2007). https://doi.org/10.1134/S1070428007080088

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  • DOI: https://doi.org/10.1134/S1070428007080088

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