Synthesis of cyclohexane derivatives including Br,Cl, N,O, and S at 1,2,4,5-positions: selectivity in addition reactions |
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Authors: | Afşin Ahmet Kaya Abdullah Menzek Ertan Şahin |
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Affiliation: | 1. Department of Chemistry, Faculty of Sciences, Atatürk University, 25240 Erzurum, Turkey;2. Gümü?hane Vocational and Training School, Gümü?hane University, 29100 Gümü?hane, Turkey |
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Abstract: | Brominations of mono addition products of 1,4-cyclohexadiene with 2,4-dinitrobenzenesulfenyl chloride (RSCl) selectively gave 1R(S),2R(S),4R(S),5R(S)-4,5-dibromo-2-(2,4-dinitrophenylthio)cyclohexyl acetate and 1R(S),2R(S),4R(S),5R(S)-4,5-dibromo-2-chlorocyclohexyl)(2,4-dinitrophenylthio)sulfane. From series reactions 7-oxabicyclo[4.1.0]hept-3-ene with reagents, such as RSCl, NaN3, and H2SO4/Ac2O, six 1,2,4,5-tetrasubstituted cyclohexane derivatives including S, O, N, Cl, and Br were selectively obtained. Formations and structures of the products were discussed. |
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Keywords: | Bromination 1,4-Cyclohexadiene 2,4-Dinitrobenzenesulfenyl chloride Sulfone Sodium azide |
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