Molybdenum Pentachloride Mediated Synthesis of Spirocyclic Compounds by Intramolecular Oxidative Coupling. Issue 1 (7th December 2015)

• Record Type: Journal Article
• Authors: Schubert, Moritz; Wehming, Kathrin; Kehl, Anton; Nieger, Martin; Schnakenburg, Gregor; Fröhlich, Roland; Schollmeyer, Dieter; Waldvogel, Siegfried R.
• Is Part Of: European journal of organic chemistry. Issue 1(2016)
• Page Start: 60
• Page End: 63
• Publication Date: 2015-12-07
• Subjects: Arene coupling -- C–C coupling -- Molybdenum -- Oxidative coupling -- Spiro compounds; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501384
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The oxidative treatment of (m)ethyl 2‐aryl cinnamates equipped with methoxy groups in position 4 of the phenyl moiety promote the formation of cyclohexadienone substructures. This dealkylative oxidative C–C coupling gives access to spirocyclic compounds and avoids the construction of the corresponding phenanthrenes. Furthermore, the transformation can be expanded to other spirocyclic systems. Abstract : The dealkylative oxidative coupling of 2‐aryl cinnamates containing a methoxy group results in the formation of spirocyclic products. Solely the position of the methoxy group determines that spiro compounds are formed upon treatment with molybdenum pentachloride and not the analogous phenanthrene products.