1095616-53-7Relevant academic research and scientific papers
A facile synthesis of a spironitrone and a study of its cycloaddition and nuoleophilic addition reactions
Crimmins, Daryl,Dimitrov, Ivaylo,O'Connor, Patrick D.,Caprio, Vittorio,Brimble, Margaret A.
experimental part, p. 3319 - 3325 (2009/05/11)
The synthesis of spironitrone 5 via microwave-assisted intramolecular alkylation of bromo oxime 10 is reported. The bromo oxime is prepared by alkylation of methyl cyclohexanecarboxylate with 1,4-dibromobutane followed by conversion of the methyl ester to an oxime. Spironitrone 5 undergoes facile 1,3-dipolar cycloaddition to a range of olefins to form a range of spirocyclic isoxazolidines. Nucleophilic addition of several Grignard reagents to spironitrone 5 provided access to a series of alkyl-substituted spirohydroxylamines.
