Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation |
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Authors: | Shveta PandiancherriDavid W Lupton |
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Institution: | School of Chemistry, Monash University, Clayton 3800, Victoria, Australia |
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Abstract: | Exposure of N-chloroamines to KOtBu or LDA, in the presence of PMDETA or HMPA, provides 2-azaallyl anions capable of π4s + π2s cycloaddition reactions with a range of olefins. Good yields were achieved with stabilised systems, however, they were more modest when accessing semi-stabilised 2-azaallyl anions. By modifying the reaction conditions, one-pot dehydrochlorination/allylation can also be achieved with a range of N-chloroamines. |
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Keywords: | 2-Azaallyl anion N-Chloroamine Halogen-metal exchange Allylation |
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