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Reagent used in synthesis of fused 3-methylfuransDimedone is used in organic chemistry to identify the presence of aldehyde group. It is also used as a catalyst in the formation of transition-metal complexes. Further, it is also employed in colorimetry, crystallography, luminescence and spectrophotometric analysis. In addition to this, it is used in the synthesis of naturally occurring fused 3-methylfurans.
Classical reagent for the identification and isolation of aldehydes: J. Org. Chem., 11, 95 (1946).
For conditions leading to exclusive 2-monomethylation, see: Synth. Commun., 3, 347 (1973). For direct nitration at the 2-position, see review on ɑ-nitroketones: Synthesis, 261 (1980).
Undergoes an example of an oxidative addition of 1,3-dicarbonyl compounds, mediated by CAN (Cerium(IV) ammonium nitrate, A12882), to give an alkene, e.g. with 2-methyl-2-pentene, the product is a fused dihydrofuran derivative: J. Chem. Soc., Perkin 1, 187 (1995):
A comparative study has shown that CAN is superior to Mn(OAc)3 for this type of reaction: J. Chem. Soc., Perkin 1, 1487 (1996).
Moosavi-Zare, A. R.; Zolfigol, M. A.; Zarei, M.; Zare, A.; Khakyzadeh, V. Application of silica-bonded imidazolium-sulfonic acid chloride (SBISAC) as a heterogeneous nanocatalyst for the domino condensation of arylaldehydes with 2-naphthol and dimedone. J. Mol. Liq. 2015, 211, 373-380.
Khazaei, A.; Gholami, F.; Khakyzadeh, V.; Moosavi-Zare, A. R.; Afsar, J. Magnetic core-shell titanium dioxide nanoparticles as an efficient catalyst for domino Knoevenagel-Michael-cyclocondensation reaction of malononitrile, various aldehydes and dimedone. RSC Adv. 2015, 5 (19), 14305-14310.