Radical addition reaction of bis(naphth-1,8-diyl-8-oxy)hydrophosphorane to olefins†
Corresponding Author
Kazumasa Kajiyama
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, JapanSearch for more papers by this authorDaisuke Itou
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Search for more papers by this authorYuki Hazama
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Search for more papers by this authorYusuke Yamamoto
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Search for more papers by this authorTakeshi K. Miyamoto
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Search for more papers by this authorCorresponding Author
Kazumasa Kajiyama
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, JapanSearch for more papers by this authorDaisuke Itou
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Search for more papers by this authorYuki Hazama
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Search for more papers by this authorYusuke Yamamoto
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Search for more papers by this authorTakeshi K. Miyamoto
Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Search for more papers by this authorDedicated to Professor Kin-ya Akiba on the occasion of his 75th birthday.
Abstract
In the presence of 1,1′-azobis(cyclohexanecarbonitrile) (ACHCN), the reaction of bis(naphth-1,8-diyl-8-oxy)hydrophosphorane with an equimolar amount of terminal and internal olefins gave the corresponding alkylphosphoranes. In the reactions with styrene and methyl acrylate, 2:1 olefin–hydrophosphorane adducts were obtained as a minor product. The reactions with terminal olefins were entirely regioselective and more efficient than those with internal olefins. In the absence of ACHCN, the radical addition reaction of the hydrophosphorane to terminal and internal olefins could also proceed slowly. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:538–544, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20719
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