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A facile synthesis of a spironitrone and a study of its cycloaddition and nucleophilic addition reactions.

  作者 Crimmins, Daryl;Dimitrov, Ivaylo;O'Connor, Patrick D.;Caprio, Vittorio;Brimble, Margaret A.;  
  选自 期刊  Synthesis;  卷期  2008年-20;  页码  3319-3325  
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[摘要]The synthesis of spiro nitrone I via microwave-assisted intramol. alkylation of 1-(4-bromobutyl)cyclohexanal oxime is reported. The bromo oxime is prepd. by alkylation of cyclohexanecarboxylate with Br(CH2)4Br followed by conversion of the ester to an oxime. Spiro nitrone I undergoes facile 1,3-dipolar cycloaddn. to a range of olefins to form a range of spirocyclic isoxazolidines. Nucleophilic addn. of several Grignard reagents to I provided access to a series of alkyl-substituted spiro hydroxylamines.

 
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