Regioselective electrophilic cyclization of o-ethynylbenzyl phenyl selenides to (Z)-1-methylidene-2-phenyl-1,3-dihydro-1H-benzo[c]selenophenium salts |
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| Authors: | Haruki Sashida Shoko Nakabayashi Mamoru Kaname |
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| Institution: | a Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan
b Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-Ku, Sagamihara, Kanagawa 252-0373, Japan |
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| Abstract: | o-Ethynylbenzyl phenyl selenides regioselectively reacted with trifluoromethanesulfonic acid to afford the (Z)-1-methylidene-2-phenyl-1,3-dihydro-1H-benzoc]selenophenium salts as the major products during the 5-exo-dig mode cyclization in good yields together with minor E isomers. The structure of the major (Z)-selenophenium salt was established by the single crystal X-ray crystallographic analysis using a tert-butyl derivative. |
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