Reaction products of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate and tricyclo[4.1.0.02,7]hept-1-yl phenyl sulfone with dinitrogen tetraoxide |
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Authors: | V A Vasin S G Kostryukov I Yu Bolusheva V V Razin |
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Institution: | (1) Ogarev Mordovian State University, ul. Bol’shevistskaya 68, Saransk, 430000, Russia;(2) St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia |
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Abstract: | The reaction of methyl tricyclo4.1.0.02,7]hepatne-1-carboxylate with dinitrogen tetraoxide in diethyl ether at ?10 to 0°C, followed by treatment of the reaction mixture with methanol, gave approximately equal amounts of methyl exo,syn-6,7-dinitro-and exo-6-hydroxy-syn-7-nitrobicyclo3.1.1]heptane-endo-6-carboxylates. Tricyclo4.1.0.02,7]hept-1-yl phenyl sulfone reacted with dinitrogen tetraoxide under analogous conditions to produce a mixture of diastereoisomeric exo,syn-and endo,syn-6,7-dinitro-6-phenylsulfonylbicyclo-3.1.1]heptanes and 6,6-dimethoxy-endo-7-nitrobicyclo3.1.1]heptane at a ratio of 4.5:2:1. Probable factors responsible for the different stereoselectivities in the addition of N2O4 at the central C1-C7 bond of the initial tricycloheptane compounds were discussed. The structural parameters of the dinitro ester and related dinitro sulfone were compared on the basis of the X-ray diffraction data. |
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