Synthesis of N,N-bis(3-butenyl)amines from 2-azaallyl dication synthetic equivalents and conversion to 2,3,6,7-tetrahydroazepines by ring-closing metathesis |
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Authors: | Pearson William H Aponick Aaron Dietz Amber L |
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Institution: | Department of Chemistry, The University of Michigan, Ann Arbor, Michigan, 48109-1055, USA. wpearson@berryassoc.com |
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Abstract: | N,N-Bis(3-butenyl)amines can be prepared by the double allylation of either (2-azaallyl)stannanes or (2-azaallyl)nitriles, both of which thereby act as synthetic equivalents to amine alpha,alpha'-dications (2-azaallyl dications). Allylmagnesium bromide is the reagent of choice for the double allylation of both substrates, although allyllithium also effects the double allylation of (2-azaallyl)nitriles. Ring-closing metathesis can be performed on the N-protected amines, or with in situ protonation, on the free amines to provide 2,3,6,7-tetrahydroazepines. (2-Azaallyl)nitriles can also be monoallylated to provide N-(3-butenyl)aminonitriles, whereas the double allylation of (2-azaallyl)stannanes cannot be stopped at monoallylation. (2-Azaallyl)silanes undergo monoallylation to give N-(3-butenyl)aminosilanes but do not undergo double allylation. |
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