[101933-27-1] · C8H7NO2S · 1-Nitro-2-phenylthioethylene · (MW 181.23)
Alternate Name: 1-phenylthio-2-nitroethylene.
Solubility: sol EtOH, acetone, THF, Et2O, CHCl3, CH2Cl2.
Analysis of Reagent Purity: NMR d 6.66 (d, J = 12 Hz, 1H), 7.24-7.56 (m, 5H), 8.18 (d, J = 12 Hz, 1H).
Electron-deficient alkenes substituted with nitro and phenylthio groups are useful reagents for the preparation of 1-nitroalkenes via the addition-elimination sequence. The reaction with various amines affords a general method for the synthesis of nitro enamines (eq 2).3,4 However, the reaction with alkoxides does not give 1-alkoxynitroethylenes, but gives 2,2-dialkoxynitroethanes; this affords a useful method for the synthesis of a-nitro aldehyde acetals (eq 3).5
This reagent reacts with the pyridinium salts in the presence of Triethylamine to give the indolizine (eq 4)6 via the azomethine ylide.
Although this reagent undergoes the Diels-Alder reaction with reactive dienes (eq 5),3 its reactivity is low compared to that of the corresponding sulfoxide and sulfone.
Oxidation of this reagent with m-Chloroperbenzoic Acid gives 1-phenylsulfinyl-2-nitroethylene, which is an excellent dienophile and acts as a nitroacetylene equivalent in the Diels-Alder reaction (eq 6).7
Ehime University, Matsuyama, Japan