Reactivity patterns of benzhydryl(mesityl)phosphane oxide – a potential intermediate in carbonyl-carbonyl coupling reactions?

References

• Marder, S. R.; Beratan, D. N.; Cheng, L. T. Approaches for Optimizing the First Electronic Hyperpolarizability of Conjugated Organic Molecules. Science 1991, 252, 103–106.
   PubMed Web of Science ®Google Scholar
• De Filippis, B.; Ammazzalorso, A.; Fantacuzzi, M.; Giampietro, L.; Maccallini, C.; Amoroso, R. Anticancer Activity of Stilbene-based Derivatives. Chem. Med. Chem. 2017, 12, 558–570.
   Google Scholar
• Manfredi, N.; Cecconi, B.; Abbotto, A. Multi-Branched Multi-Anchoring Metal-Free Dyes for Dye-Sensitized Solar Cells. Eur. J. Org. Chem. 2014, 2014, 7069–7086.
   Web of Science ®Google Scholar
• Larder, D. F.; Kluge, F. F. Alexander Mikhailovich Butlerov's Theory of Chemical Structure. J. Chem. Educ. 1971, 48, 287–289.
   Web of Science ®Google Scholar
• Bissember, A. C.; Levina, A.; Fu, G. C. A Mild, Palladium-Catalyzed Method for the Dehydrohalogenation of Alkyl Bromides: Synthetic and Mechanistic Studies. J. Am. Chem. Soc. 2012, 134, 14232–14237.
   PubMed Web of Science ®Google Scholar
• Friesen, J. B.; Schretzman, R. Dehydration of 2-Methyl-1-Cyclohexanol: New Findings from a Popular Undergraduate Laboratory Experiment. J. Chem. Educ. 2011, 88, 1141–1147.
   Web of Science ®Google Scholar
• Enders, D.; Knopp, M.; Schiffers, R. Asymmetric [3.3]-Sigmatropic Rearrangements in Organic Synthesis. Tetrahedron: Asymmetry 1996, 7, 1847–1882.
   Google Scholar
• Staden, L. F. v.; Gravestock, D.; Ager, D. New Developments in the Peterson Olefination Reaction. Chem. Soc. Rev. 2002, 31, 195–200.
   PubMed Web of Science ®Google Scholar
• Wittig, G. From Diyls to Ylides to my Idyll. Science 1980, 210, 600–604.
   PubMed Web of Science ®Google Scholar
• Boutagy, J.; Thomas, R. Olefin Synthesis with Organic Phosphonate Carbanions. Chem. Rev. 1974, 74, 87–99.
   Web of Science ®Google Scholar
• Esfandiarfard, K.; Mai, J.; Ott, S. Unsymmetrical E-Alkenes from the Stereoselective Reductive Coupling of Two Aldehydes. J. Am. Chem. Soc. 2017, 139, 2940–2943.
   PubMed Web of Science ®Google Scholar
• Mai, J.; Arkhypchuk, A. I.; Gupta, A. K.; Ott, S. Reductive Coupling of Two Aldehydes to Unsymmetrical E-Alkenes via Phosphaalkene and Phosphinate Intermediates. Chem. Commun. (Camb.) 2018, 54, 7163–7166.
   PubMed Web of Science ®Google Scholar
• Arkhypchuk, A. I.; D'Imperio, N.; Ott, S. One-Pot Intermolecular Reductive Cross-Coupling of Deactivated Aldehydes to Unsymmetrically 1,2-Disubstituted Alkenes. Org. Lett. 2018, 20, 5086–5089.
   PubMed Web of Science ®Google Scholar
• McMurry, J. E. Carbonyl-Coupling Reactions Using Low-Valent Titanium. Chem. Rev. 1989, 89, 1513–1524.
   Web of Science ®Google Scholar
• Christiansen, A.; Li, C.; Garland, M.; Selent, D.; Ludwig, R.; Spannenberg, A.; Baumann, W.; Franke, R.; Börner, A. On the Tautomerism of Secondary Phosphane Oxides. Eur. J. Org. Chem. 2010, 2010, 2733–2741.
   Web of Science ®Google Scholar
• Kurscheid, B.; Wiebe, W.; Neumann, B.; Stammler, H. G.; Hoge, B. Investigations of the Tautomeric Equilibria between Phosphane Oxides and Their Corresponding Phosphinous Acids Bearing Electron-Withdrawing Perfluoroaryl Groups. Eur. J. Inorg. Chem. 2011, 2011, 5523–5529.
   Google Scholar
• Wang, S.; Samedov, K.; Serin, S. C.; Gates, D. P. PhP = CPh 2 and Related Phosphaalkenes: A Solution Equilibrium Between a Phosphaalkene and a 1,2-Diphosphetane. Eur. J. Inorg. Chem. 2016, 2016, 4144–4151.
   Google Scholar
• Van Der Knaap, T. A.; Klebach, T. C.; Visser, F.; Bickelhaupt, F.; Ros, P.; Baerends, E. J.; Stam, C. H.; Konijn, M. Synthesis and Structure of Aryl-Substituted Phospha-Alkenes. M. Tetrahedron 1984, 40, 765–776.
   Web of Science ®Google Scholar
• Van der Knap, T. A.; Bickelhaupt, F. A Nucleophilic Reaction of a Phosphaalkene: The Methylation of Mesityldiphenylmethylenephosphine. Tetrahedron Lett. 1982, 23, 2037–2040.
   Web of Science ®Google Scholar
• Bi Jie, L.; Yi Zhou, L.; Xing Yu, L.; Jia, L.; Bing Tao, G.; Zhang Jie, S. Cross-Coupling of Aryl/Alkenyl Pivalates with Organozinc Reagents through Nickel-Catalyzed C-O Bond Activation under Mild Reaction Conditions. Angew. Chem. Int. Ed. Engl. 2008, 47, 10124–10127.
   PubMed Web of Science ®Google Scholar