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[4+2]-Cyclodimer of sabinone: formation,crystal structure,and NMR spectra
Authors:Suleimenov  E. M.  Raldugin  V. A.  Shakirov  M. M.  Bagryanskaya  I. Yu.  Gatilov  Yu. V.  Kulyjiasov  A. T.  Adekenov  S. M.
Affiliation:(1) Institute of Phytochemistry, Ministry of Education and Sciences of the Republic of Kazakhstan, 4 ul. M. Gazalieva, 470032 Karaganda, Kazakhstan;(2) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent"eva, 630090 Novosibirsk, Russian Federation
Abstract:Oxidation of (+)-sabinol, (1S,3R,5S)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol, by active MnO2 afforded not the expected sabinone but only its [4+2]-cyclodimer. The molecular structure of the latter was established by X-ray diffraction analysis. The 1H and 13C NMR spectra of this cyclodimer were interpreted using 2D NMR spectroscopy.
Keywords:(+)-sabinol  (1S,3R,5S)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol  oxidation  sabinone  in situ [4+2]-cyclodimerization  X-ray diffraction analysis  2D NMR spectroscopy
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