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The reactivity of N,N-dialkyl-N-(3-phenylsulfinyltetrahydrofuran-2-ylidene)ammonium bromide |
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| Authors: | T M Ugurchieva A V Lozanova M V Zlokazov V V Veselovsky |
| Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
| Abstract: | trans-Stereoselective electrophilic cyclization of (2R*,SS*)-N, N-diisopropyl-2-phenylsulfinylpent-4-enamide under the action of bromine afforded (3R*,5S*, SS*)-N-(5-bromomethyl-3-phenylsulfinyltetrahydrofuran-2-ylidene)-N,N-diisopropylammonium bromide. Its transformations under the conditions of hydrolysis, dehydrobromination, and hydride reduction were studied. Dedicated to Academician V. A. Tartakovsky on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1485–1490, August, 2007. |
| Keywords: | (2R* SS*)-N N-diisopropyl-2-phenylsulfinylpent-4-enamide bromocyclization iminium compounds (3R* 5S* SS*)-N-(5-bromomethyl-3-phenylsulfinyltetrahydrofuran-2-ylidene)-N N-diisopropylammonium bromide hydrolysis hydride reduction |
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