Synthesis of cyclohexane derivatives including Br, Cl, N, O, and S at 1,2,4,5-positions: selectivity in addition reactions

Brominations of mono addition products of 1,4-cyclohexadiene with 2,4-dinitrobenzenesulfenyl chloride (RSCI) 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. (C) 2013 Elsevier Ltd. All rights reserved.