1082-18-4Relevant academic research and scientific papers
Reactions of (1-nitroethenyl)sulfonylbenzene, a nitroethene derivative geminally substituted by a second W-group
Wade, Peter A.,Murray, James K.,Pipic, Alma,Arbaugh, Robert J.,Jeyarajasingam, Amutha
, p. 337 - 342 (2009)
Nitroaldol reaction of phenylsulfonylnitromethane with formaldehyde affords a mixture of 2, 4-dinitro-2, 4-bis (phe-nylsulfonyl)butan-1-ol and 2, 4-dinitro-2, 4- bis (phenylsulfonyl)pentane-1, 5-diol. Treatment of this mixture with base followed by reacidification affords 1,1′-[(1, 3-dinitro-1, 3-propanediyl)bis (sulfonyl)]bis (benzene) as a mixture of (R*, R*) and (R*, S*)- diastereomers from which the (R*, S*)- diastereomer can be obtained pure. The intermediate in the nitroaldol reaction is (1-nitroethenyl)sulfonylbenzene and, if dienes are present, additional products are also obtained. If either (E)-2-methyl-1, 3-pentadiene or 1-(1-methylethenyl)cyclohexene are present, typical Diels-Alder adducts are obtained with the major isomers explainable by assuming a transition state in which the nitro group is endo. If furan is present, its formal conjugate addition product, 2-[2-nitro-2-(phenylsulfonyl)ethyl]furan, is formed. If cyclooctatetraene is present, it first dimerizes and then affords isomeric Diels-Alder cycloadducts of the dimer. Semiempirical calculations comparing the LUMO energies of (1-nitroethenyl)sulfonylbenzene to the corresponding trans-1,2 isomer are presented to explain relative reactivity of 1, 1- and 1, 2-disubstituted dienophiles. Copyright
