Abstract
A method was developed for the synthesis of 6,7-benzo-3-borabicyclo[3.3.1]nonane and 6,7-benzo-3-azabicyclo[3.3.1]nonane derivatives based on intramolecular cyclization of 2-allylphenyl(diallyl)borane. Intramolecular arylboration of the double bond in 1,5-diallyl-2,3-benzo-1-boracyclohexane was carried out for the first time. Conventional oxidation (H2O2-OH−) of 6,7-benzo-3-methoxy-3-borabicyclo[3.3.1]nonane afforded cis-1,3-di(hydroxymethyl) tetralin. The structure of the latter was established by X-ray diffraction analysis.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 668–672, March, 2005.
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Kuznetsov, N.Y., Starikova, Z.A., Averkiev, B.B. et al. Synthesis of 6,7-benzo-3-borabicyclo[3.3.1]nonane and its 3-aza analog from 2-allylphenyl(diallyl)borane. Intramolecular arylboration of the C=C bond. Russ Chem Bull 54, 678–683 (2005). https://doi.org/10.1007/s11172-005-0305-5
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DOI: https://doi.org/10.1007/s11172-005-0305-5