Comparison of reactivities of 1- and 4-oxotetrahydrocarbazoles in reactions with nucleophilic and electrophilic reagents |
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Authors: | S Yu Kukushkin P Yu Ivanov L M Alekseeva V I Levina K I Kobrakov N B Grigor'ev V G Granik |
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Institution: | (1) State Research Center of Antibiotics, 3a ul. Nagatinskaya, 117003 Moscow, Russian Federation;(2) A. N. Kosygin Moscow State Textile Academy, 1 ul. Malaya Kaluzhskaya, 119991 Moscow, Russian Federation |
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Abstract: | The half-wave potentials of polarographic reduction of the carbonyl group in unsubstituted and N-methyl- and N-phenylsulfonyl-substituted 1- and 4-oxotetrahydrocarbazoles and their reactivities in reactions with nucleophilic (NaBH4, malonodinitrile, and cyanoacetamide) and electrophilic (DMF dimethyl acetal) reagents were compared. 4-Oxotetrahydrocarbazoles
are much less reactive than 1-oxotetrahydrocarbazoles.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1832–1836, August, 2005. |
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Keywords: | 1 2 3 9-tetrahydro-4H-carbazol-4-ones 2 3 4 9-tetrahydro-1H-carbazol-1-ones reduction voltammetry dimethylformamide dimethyl acetal |
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