title: Electron-deficient 1- and 2-azabuta-1,3-dienes: a comprehensive survey of their synthesis and reactivity.
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).
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Gent, Belgium.
authors.forename: Jean-Christophe M
authors.initials: JC
authors.lastname: Monbaliu
authors.forename: Kurt G R
authors.initials: KG
authors.lastname: Masschelein
authors.forename: Christian V
authors.initials: CV
authors.lastname: Stevens
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002070:Butadienes / Q000737:chemistry*; D004583:Electrons; D055601:Organic Chemistry Phenomena
chemical_list: D001372:Aza Compounds; D002070:Butadienes