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Synthesis 1992; 1992(4): 355-357
DOI: 10.1055/s-1992-26106
short paper
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Amberlyst A 21 as New and Efficient Surface Catalyst for the Cleavage of 2-Nitrocycloalkanones

Roberto Ballini* , Marino Petrini, Valeria Polzonetti
  • *Dipartimento di Scienze Chimiche, Via S. Agostino 1, I-62032 Camerino, Italy
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Publication Date:
17 September 2002 (online)

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Ring cleavage of 2-Nitrocycloalkanones with methanol/Amberlyst A 21 gave methyl ω-nitroalkanoates, O2NCH2(CH2)nCO2Me where n = 3-6, 8-10, 13, in high yield. Subsequent Nef reaction gave the corresponding ω-oxo compounds which were isolated, in the case of methyl 7-oxoheptanoate and methyl 8-oxooctanoate only, or reduced directly with sodium borohydride to give ω-hydroxyalkanoates. A new formal synthesis of exaltolide (15-pentadecanolide) is also reported.