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Issue 9, 2011
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Electron-deficient 1- and 2-azabuta-1,3-dienes: a comprehensive survey of their synthesis and reactivity

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Abstract

Electron-deficient 1- and 2-azabuta-1,3-dienes are reagents intrinsically able to provide a wide range of cyclic and acyclic N-containing building blocks. Depending on their substitution, they behave as dienes for Diels–Alder reactions, as partners for [4+1], [3+2], [2+2]-cycloadditions, for aziridinations and as electrophiles for 1,2 and 1,4-additions. Nowadays, they are a very versatile family of compounds, despite their usual instability and complex reactivity. Four decades of research in this challenging area are reviewed in this critical review: their synthetic aspects and their reactivity towards a wide range of dienophiles, dipoles and nucleophiles are described as well. The introduction focuses on their electronic properties in order to get a clear picture of their reactivity (190 references).

Graphical abstract: Electron-deficient 1- and 2-azabuta-1,3-dienes: a comprehensive survey of their synthesis and reactivity

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Article information


Submitted
17 Mar 2011
First published
07 Jun 2011

Chem. Soc. Rev., 2011,40, 4708-4739
Article type
Critical Review

Electron-deficient 1- and 2-azabuta-1,3-dienes: a comprehensive survey of their synthesis and reactivity

J. M. Monbaliu, K. G. R. Masschelein and C. V. Stevens, Chem. Soc. Rev., 2011, 40, 4708
DOI: 10.1039/C1CS15070G

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