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

The Journal of Organic Chemistry
William H PearsonAmber L Dietz

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.

References

Aug 23, 2002·Chemical Communications : Chem Comm·Andrew S EdwardsJoseph P A Harrity
Oct 12, 2002·The Journal of Organic Chemistry·Alan R KatritzkyAlina Silina
Dec 12, 2002·Journal of the American Chemical Society·Peter WipfHidenori Takahashi
Jul 24, 2003·Chemical Society Reviews·Reinhard W Hoffmann
Dec 6, 2003·The Journal of Organic Chemistry·Steven H L VerhelstJacques H van Boom

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Citations

Jan 26, 2013·Chemical Reviews·Bagher Eftekhari-SisAli Akbari
Sep 9, 2015·The Journal of Organic Chemistry·Mitsuhiro YoshimatsuOsamu Muraoka
Aug 14, 2009·Organic & Biomolecular Chemistry·Dhevalapally B RamacharyKinthada Ramakumar
Sep 15, 2010·Chemistry, an Asian Journal·Viktor KolmanVladimir Sindelar
Oct 12, 2018·Chemical Reviews·Shaojian TangJason J Chruma

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