Cyclizations and rearrangements of samarium diiodide-generated vinyl radicals

…, PC Montevecchi, ML Navacchia

文献索引：Capella, Laura; Montevecchi, Pier Carlo; Navacchia, Maria Luisa Journal of Organic Chemistry, 1995 , vol. 60, # 23 p. 7424 - 7432

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被引用次数: 32

摘要

Vinyl bromides 1, 5, 15, 20, 23, 27, 33a, b, 41a-c, 44a-c, 46a, b, 52a, b, 55a, 56a, b, and 60a, b react with samarium diiodide in THF and/or acetonitrile to give the corresponding vinyl radicals. Radicals 3, 7, and 16 afforded products deriving from cyclization on the adjacent triple bond in a 5-(x-exo)-em, 6-(xendo) exo, and 6-(x-exo) exo mode, respectively. Radical 7 undergoes competitive 1, 5-hydrogen translocation. Vinyl radicals 21 and 24 readily ...