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Synlett 1991; 1991(11): 805-807
DOI: 10.1055/s-1991-20883
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Samarium(II) Iodide Mediated Cyclizations of Alkynyl Halides

Sharon M. Bennett* , Denis Larouche
  • *Département de chimie, Université du Québec à Montréal, C.P. 8888, succursale A, Montréal, Québec H3C 3P8, Canada
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Publication Date:
07 March 2002 (online)

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Alkynyl halides (6-halo-1-ynes) react with samarium(II) iodide (SmI2) in refluxing tetrahydrofuran to give cyclized products (methylenecyclopentanes) in good yields. Results from deuterium oxide quenching experiments are consistent with the presence of radical species as reaction intermediates. The use of 1, 3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) as a cosolvent results in slightly better yields and it also alters the steps involved in the transformation of unsaturated bromides to the cyclized products.