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Imination of (<jats:italic>R<\/jats:italic>)\u2010methyl <jats:italic>p<\/jats:italic>\u2010tolyl sulfoxide proceeded with predominant retention of configuration at the stereogenic sulfur center. The Hammett plot afforded <jats:italic>\u03c1<\/jats:italic> values of \u22120.58 for <jats:italic>para<\/jats:italic>\u2010substituted thioanisoles and \u22120.49 for their equivalent sulfoxides, which suggests a buildup of positive charge on the sulfur atoms of sulfides and sulfoxides in the transition state. Calculations suggest a bimolecular nucleophilic\u2010substitution mechanism on the negatively charged nitrogen atom of the sulfonylimino\u2010\u03bb<jats:sup>3<\/jats:sup>\u2010bromane, which involves the attack of a sulfide from the opposite side to bromine(III).<\/jats:p>","DOI":"10.1002\/chem.201000759","type":"journal-article","created":{"date-parts":[[2010,6,22]],"date-time":"2010-06-22T01:43:57Z","timestamp":1277171037000},"page":"8713-8718","source":"Crossref","is-referenced-by-count":41,"title":["Imination of Sulfides and Sulfoxides with Sulfonylimino\u2010\u03bb<sup>3<\/sup>\u2010Bromane under Mild, Metal\u2010Free Conditions"],"prefix":"10.1002","volume":"16","author":[{"given":"Masahito","family":"Ochiai","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masao","family":"Naito","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazunori","family":"Miyamoto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Satoko","family":"Hayashi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Waro","family":"Nakanishi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2010,7,29]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"Reviews:"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2003-41010"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020043t"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr800332c"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.2174\/1385272053765024"},{"key":"e_1_2_6_6_2","volume-title":"Hypervalent Iodine Chemistry","year":"2003"},{"key":"e_1_2_6_7_2","first-page":"1","volume":"18","author":"Du Bois J.","year":"2005","journal-title":"Chemtracts"},{"key":"e_1_2_6_8_2","volume-title":"Modern Rhodium\u2010Catalyzed Organic Reactions","author":"Espino C. 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Ochterski P.\u2005Y. Ayala K. Morokuma G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg V.\u2005G. Zakrzewski S. Dapprich A.\u2005D. Daniels M.\u2005C. Strain O. Farkas D.\u2005K. Malick A.\u2005D. Rabuck K. Raghavachari J.\u2005B. Foresman J.\u2005V. Ortiz Q. Cui A.\u2005G. Baboul S. Clifford J. Cioslowski B.\u2005B. Stefanov G. Liu A. Liashenko P. Piskorz I. Komaromi R.\u2005L. Martin D.\u2005J. Fox T. Keith M.\u2005A. Al\u2010Laham C.\u2005Y. Peng A. Nanayakkara M. Challacombe P.\u2005M.\u2005W. Gill B. Johnson W. Chen M.\u2005W. Wong C. Gonzalez J.\u2005A. Pople Gaussian Inc. 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