Formation of Substituted Oxa‐ and Azarhodacyclobutanes. Issue 50 (6th November 2013)

• Record Type: Journal Article
• Authors: Dauth, Alexander; Rigling, Carla; Tsoung, Jennifer; Love, Jennifer A.
• Is Part Of: Chemistry. Volume 19:Issue 50(2013)
• Page Start: 17180
• Page End: 17191
• Publication Date: 2013-11-06
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201302421
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The preparation of substituted oxa‐ and azarhodacyclobutanes is reported. After exchange of ethylene with a variety of unsymmetrically and symmetrically substituted alkenes, the corresponding rhodium–olefin complexes were oxidized with H₂O₂ and PhINTs (Ts=<italic>p</italic>‐toluenesulfonyl) to yield the substituted oxa‐ and azarhodacyclobutanes, respectively. Oxarhodacyclobutanes could be prepared with excellent selectivity for incorporation of the oxygen atom on the more substituted carbon atom of the alkene. At the same time, azarhodacyclobutanes showed good‐to‐excellent selectivity for heteroatom incorporation on the less substituted carbon. Furthermore, it was shown that steric modifications of the ancillary ligand have a significant influence on the selectivity of Rh–olefin complex formation as well as formation of the substituted azametallacycles.</p> </abstract>