B(C6F5)3‐Mediated Transformations and Hydrogenation of Carbodiimides. Issue 5 (26th November 2014)

• Record Type: Journal Article
• Authors: Holthausen, Michael H.; Colussi, Mariah; Stephan, Douglas W.
• Is Part Of: Chemistry. Volume 21:Issue 5(2015)
• Page Start: 2193
• Page End: 2199
• Publication Date: 2014-11-26
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201405014
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The reactivity of a series of carbodiimides RNCNR (R=<italic>t</italic>Bu (<bold>1 a</bold>), <italic>i</italic>Pr (<bold>1 b</bold>), SiMe₃ (<bold>1 c</bold>), and Dipp (2, 6‐di‐<italic>iso</italic>‐propylphenyl (<bold>1 d</bold>)) with B(C₆F₅)₃ was investigated. After initial adduct formation, several distinct reaction pathways were identified. These pathways involve either isomerization of the carbodiimide to cyanamide derivatives or insertion of a carbodiimide into a BC bond of B(C₆F₅)₃ to yield four‐membered heterocycles. In the presence of dihydrogen, stepwise hydrogenation of the heteroallene moiety in the carbodiimides was achieved, which yielded the respective amidine–B(C₆F₅)₃ adducts and amidinium borate salts upon reaction with one or two equivalents of H₂, respectively.</p> </abstract>