[101933-29-3] · C8H7NO4S · 1-Nitro-2-phenylsulfonylethylene · (MW 213.23)
Alternate Name: 1-phenylsulfonyl-2-nitroethylene.
Physical Data: mp 148-150 °C.
Solubility: sol THF, Et2O, CHCl3, CH2Cl2.
Analysis of Reagent Purity: IR 1160, 1350, 1550 cm-1; NMR d 7.50-7.96.
Preparative Method: by oxidation of 1-Nitro-2-phenylthioethylene with m-Chloroperbenzoic Acid (2 equiv).2
Addition-elimination reactions of various nucleophiles to this reagent provide a useful method for the preparation of various 1-nitroalkenes. Polyfunctional organozinc and copper reagents react with this reagent to give polyfunctional 1-nitroalkenes. Organometallics bearing an ester (eq 1),3 diene (eq 2),4 or oxygen function (eq 3)5 give terminal nitroalkenes substituted with these functional groups. Thus a precursor for an intramolecular Diels-Alder reaction and new allylic acetates bearing terminal nitroalkenes are readily prepared by this procedure.
This reagent is an excellent dienophile in the Diels-Alder reaction and reacts with various dienes to give the adducts under mild conditions. Subsequent treatment of the resulting b-nitro sulfones with Tri-n-butylstannane results in the reductive elimination of the nitro and sulfonyl groups6 to give 1,4-cyclohexadienes. Thus this reagent serves as a very reactive Acetylene equivalent,7 and various dienes have been converted into 1,4-cyclohexadienes by this procedure (eqs 4 and 5).8,9
Ehime University, Matsuyama, Japan