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The nitro-group is susceptible to nucleophilic displacement (compare 1,4-Dinitrobenzene, A10293): J. Heterocycl. Chem., 18, 1241 (1981). This has been used as the basis of a synthesis of diaryl ethers involving Diels-Alder addition and decarboxylative aromatization of the adduct: J. Chem. Soc., Perkin 1, 1231 (1990):/n
Undergoes vicarious nucleophilic substitution of hydrogen at the 3-position. For example with chloromethyl phenyl sulfone and base, 2-nitro-3-(phenylsulfonylmethyl)furan is formed in 75% yield: Tetrahedron, 51, 8339 (1995). For analogous example and reaction scheme, see 2-Nitrothiophene, A17464./n
For a review of vicarious nucleophilic substitution in heterocyclic compounds, see: Synthesis, 103 (1991)./n
Hazard Statements: H341
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