[3 + 2] and [5 + 2] Arene–Alkene Photocycloadditions
1991; Elsevier BV; Linguagem: Inglês
10.1016/b978-0-08-052349-1.00135-9
AutoresPaul A. Wender, Lorenz Siggel, John M. Nuss,
Tópico(s)Organic Chemistry Cycloaddition Reactions
ResumoArene-alkene cycloadditions (Scheme 1) are among the most theoretically intriguing and synthetically promising recent discoveries in organic chemistry, providing particularly efficient synthetic access to a range of natural and non-natural compounds from simple, readily available precursors.1 Reflecting their enormous versatility and their consequent designation in this series as higher order cycloadditions, these reactions have the unique capability of producing from three- to nine-membered rings through [2C + 2C], [3C + 2C], [4C + 2C], [5C + 2C], [6C + 2C], [4C + 3C], [4C + 4C] and [5C + 4C] conjunctions of arenes with various π-systems. In this chapter, an overview of this fascinating class of reactions will be presented. In accord with the goals and focus of this series, emphasis will be placed on developments of the last decade and on the unique role of these reactions in organic synthesis. Primary attention will be given to the meta cycloaddition reaction due to its more extensive development and use in synthesis. As a consequence of the inexorable relationship between synthesis and mechanism, this treatment will start with a brief historical perspective and mechanistic analysis.
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