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Reactions of \u03b1\u2010alkoxyphosphonium salts, prepared from various acetals and tris(<jats:italic>o<\/jats:italic>\u2010tolyl)phosphine, with a variety of nucleophiles proceeded efficiently. These processes represent the first examples of high\u2010yielding nucleophilic substitution reactions of \u03b1\u2010alkoxyphosphonium salts. The reactivity of these salts was determined by a balance between steric and electronic factors, respectively, represented by cone angles <jats:italic>\u03b8<\/jats:italic> and CO stretching frequencies <jats:italic>\u03bd<\/jats:italic> (steric and electronic parameters, respectively). In addition, a novel reaction of \u03b1\u2010alkoxyphosphonium salts derived from Ph<jats:sub>3<\/jats:sub>P with Grignard reagents was observed to take place in the presence of O<jats:sub>2<\/jats:sub> to afford alcohols in good yields. A radical mechanism is proposed for this process that has gained support from isotope\u2010labeling and radical\u2010inhibition experiments.<\/jats:p>","DOI":"10.1002\/chem.201200480","type":"journal-article","created":{"date-parts":[[2012,7,24]],"date-time":"2012-07-24T15:58:36Z","timestamp":1343145516000},"page":"11423-11432","source":"Crossref","is-referenced-by-count":16,"title":["Effects of Phosphorus Substituents on Reactions of \u03b1\u2010Alkoxyphosphonium Salts with Nucleophiles"],"prefix":"10.1002","volume":"18","author":[{"given":"Akihiro","family":"Goto","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kazuki","family":"Otake","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ozora","family":"Kubo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoshinari","family":"Sawama","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tomohiro","family":"Maegawa","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiromichi","family":"Fujioka","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,7,24]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)91403-6"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)85281-8"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1990-21007"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1992-26168"},{"key":"e_1_2_6_6_2","unstructured":"For recent applications in total synthesis see:"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol027389a"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0347361"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.04.033"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo051479m"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol901455q"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol102169w"},{"key":"e_1_2_6_13_2","unstructured":"\u00a0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja046103p"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja060328d"},{"key":"e_1_2_6_16_2","unstructured":"\u00a0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-951509"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-06-S(K)46"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo071187g"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-08-S(D)69"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc00170h"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc13919c"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60307a002"},{"key":"e_1_2_6_24_2","unstructured":"See the Supporting Information for details."},{"key":"e_1_2_6_25_2","unstructured":"The \u03b1\u2010alkoxyphosphonium salts prepared from Ph3P were stable and easily isolated but they are highly polar compounds and cannot be easily handled; 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