141
Views
0
CrossRef citations to date
0
Altmetric
Articles

Theoretical consideration on phosphorus–oxygen bond formation of sterically crowded triarylphosphines and their radical cations

ORCID Icon
Pages 468-473 | Received 02 Nov 2021, Accepted 25 Nov 2021, Published online: 16 Dec 2021

References

  • Halpern, E. J.;Mislow, K. Conformational Analysis of Tritolyphosphines. J. Am. Chem. Soc. 1967, 89, 5224–5228. DOI: 10.1021/ja00996a025.
  • Stepanov, B. I.;Karpova, E. N.;Bokanov, A. I. Synthesis of Trimesitylphosphine and Tetramesityldiphosphine. J. Gen. Chem. USSR 1969, 39, 1544–1549.
  • Blount, J. F.;Maryanoff, C. A.;Mislow, K. Molecular Structure of Trimesitylphosphine: An Unprecedented Enlargement of Valence Bond Angles in a Phosphine. Tetrahedron Lett. 1975, 48, 913–916. DOI: 10.1016/S0040-4039(00)72018-1.
  • Culcasi, M.;Berchadsky, Y.;Gronchi, G.;Tordo, P. Anodic Behavior of Crowded Triarylphosphines. ESR Study of Triarylphosphoniumyl Radicals, Ar3P.•+. J. Org. Chem. 1991, 56, 3537–3542. DOI: 10.1021/jo00011a018.
  • Il’yasov, A. V.;Kargin, Y. M.;Vafina, A. A. ESR Spectra of Electrochemically Generated Radical Ions. Russ. J. Gen. Chem 1994, 63, 1833–1840.
  • Palau, C.;Berchadsky, Y.;Chalier, F.;Finet, J.-P.;Gronchi, G.;Tordo, P. Tris(Monochlorophenyl)- and Tris(Dichlorophenyl)Phosphines: Molecular Geometry, Anodic Behavior, and ESR Studies. J. Phys. Chem. 1995, 99, 158–163. DOI: 10.1021/j100001a028.
  • Merzougui, B.;Berchadsky, Y.;Tordo, P.;Gronchi, G. Trimesityl Phosphoniumyl Cation Radical: Electrogeneration and Evolution. Electrochim. Acta. 1997, 42, 2445–2453. DOI: 10.1016/S0013-4686(96)00427-6.
  • Zagumennov, V. A.;Nikitin, E. V. Reactivity of Radical Cations of Trimesitylphosphine. Russ. J. Electrochem 2003, 1236–1239.
  • Ménard, G.;Hatnean, J. A.;Cowley, H. J.;Lough, A. J.;Rawson, J. M.;Stephan, D. W. C–H Bond Activation by Radical Ion Pairs Derived from R3P/Al(C6F5)3 Frustrated Lewis Pairs and N2O. J. Am. Chem. Soc. 2013, 135, 6446–6449. DOI: 10.1021/ja402964h.
  • Sasaki, S.;Sutoh, K.;Murakami, F.;Yoshifuji, M. Synthesis, Structure, and Redox Properties of the Extremely Crowded Triarylpnictogens: Tris(2,4,6-Triisopropylphenyl)Phosphine, Arsine, Stibine, and Bismuthine. J. Am. Chem. Soc. 2002, 124, 14830–14831. DOI: 10.1021/ja027493n.
  • Boeré, R. T.;Zhang, Y. Extremely Bulky Triarylphosphines Incorporating 2,6-Diisopropylphenyl Substituents; Consideration of Steric Shielding and Steric Pressure. J. Organomet. Chem 2005, 690, 2651–2657. DOI: 10.1016/j.jorganchem.2004.11.043.
  • Sasaki, S.;Yoshifuji, M. Synthesis, Structure and Properties of Crowded Triarylphosphines. COC. 11, 17–31. DOI: 10.2174/138527207779316507.
  • Boeré, R. T.;Bond, A. M.;Cronin, S.;Duffy, N. W.;Hazendonk, P.;Masuda, J. D.;Pollard, K.;Roemmele, T. L.;Tran, P.;Zhang, Y. Photophysical, Dynamic and Redox Behavior of Tris(2,6-Diisopropylphenyl)Phosphine. New J. Chem. 2008, 32, 214–231. DOI: 10.1039/B709602J.
  • Bullock, J. P.;Bond, A. M.;Boeré, R. T.;Gietz, T. M.;Roemmele, T. L.;Seagrave, S. D.;Masuda, J. D.;Parvez, M. Synthesis, Characterization, and Electrochemical Studies of PPh3-n(dipp) (dipp = 2,6-Diisopropylphenyl): Steric and Electronic Effects on the Chemical and Electrochemical Oxidation of a Homologous Series of Triarylphosphines and the Reactivities of the Corresponding Phosphoniumyl Radical Cations. J. Am. Chem. Soc. 2013, 135, 11205–11215. DOI: 10.1021/ja403555d.
  • Pan, X.;Chen, X.;Li, T.;Li, Y.;Wang, X. Isolation and X-Ray Crystal Structures of Triarylphosphine Radical Cations. J. Am. Chem. Soc. 2013, 135, 3414–3417. DOI: 10.1021/ja4012113.
  • Sasaki, S.;Sutoh, K.;Shimizu, Y.;Kato, K.;Yoshifuji, M. Oxidation of Tris(2,4,6-Triisopropylphenyl)Phosphine and Arsine. Tetrahedron Lett. 2014, 55, 322–325. DOI: 10.1016/j.tetlet.2013.11.004.
  • Sasaki, S. Reaction of a Sterically Crowded Triarylphosphine with Iodine in the Presence of Oxygen. Phosphorus, Sulfur Silicon Relat. Elem. 2016, 191, 1513–1514. DOI: 10.1080/10426507.2016.1212344.
  • Sasaki, S.;Murakami, F.;Murakami, M.;Watanabe, M.;Kato, K.;Sutoh, K.;Yoshifuji, M. Synthesis of Crowded Triarylphosphines Carrying Functional Sites. J. Organomet. Chem. 2005, 690, 2664–2672. dDOI: 10.1016/j.jorganchem.2004.10.031.
  • Sutoh, K.;Sasaki, S.;Yoshifuji, M. Synthesis and Redox Properties of Crowded Triarylphosphines Possessing Ferrocenyl Groups. Inorg. Chem. 2006, 45, 992–998. DOI: 10.1021/ic051038l.
  • Sasaki, S.;Sasaki, K.;Yoshifuji, M. Synthesis, Structure, and Properties of Tris(2,6-Diisopropyl-4-Methoxyphenyl)Phosphine. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 410–414. DOI: 10.1080/10426500701735403.
  • Sasaki, S.;Murakami, M.;Murakami, F.;Yoshifuji, M. Synthesis and Redox Properties of Sterically Crowded Triarylphosphine and Tetraaryldiphosphane Bearing Phenothiazinyl Groups. Heteroatom Chem. 2011, 22, 506–513. DOI: 10.1002/hc.20714.
  • Sasaki, S.;Murakami, M.;Yoshifuji, M. Synthesis and Redox Properties of Sterically Crowded Triarylphosphine Bearing Two Phenothiazine Moieties. Phosphorus, Sulfur Silicon Relat. Elem. 2019, 194, 598–601. DOI: 10.1080/10426507.2018.1547728.
  • Sasaki, S.;Kato, K.;Sasaki, K.;Yoshifuji, M. Sterically Crowded Diphosphines Bearing Ethynylene and 1,2-Phenylene Linkers. Tetrahedron Lett. 2020, 61, 151366. DOI: 10.1016/j.tetlet.2019.151366.
  • Sasaki, S.;Ogawa, K.;Watanabe, M.;Yoshifuji, M. Synthesis and Properties of Sterically Crowded Triarylphosphines Bearing Naphthoquinone Moieties. Organometallics 2010, 29, 757–766. DOI: 10.1021/om900526m.
  • Sasaki, S.;Sasaki, K.;Yoshifuji, M. Synthesis, Structure, and Properties of Extended-Conjugated Systems Bearing Sterically Crowded Triarylphosphines. J. Organomet. Chem. 2011, 696, 3307–3315. DOI: 10.1016/j.jorganchem.2011.07.013.
  • Sasaki, S.;Ogawa, K.;Nakamura, K.;Yoshifuji, M.;Morita, N. Synthesis and Properties of Sterically Crowded Triarylphosphines Bearing Anthra- and Naphtho-Quinones, and Their Oligomers. J. Organomet. Chem. 2014, 751, 525–533. DOI: 10.1016/j.jorganchem.2013.10.055.
  • Sasaki, S.;Yoshifuji, M. Synthesis and Properties of a Sterically Crowded Triarylphosphine Bearing an Ester Group. Phosphorus, Sulfur Silicon Relat. Elem. 2016, 191, 507–510. DOI: 10.1080/10426507.2015.1114943.
  • Sasaki, S. Sterically Crowded Triarylphosphines Bearing Cyano Groups. Tetrahedron Lett. 2018, 59, 2251–2255. DOI: 10.1016/j.tetlet.2018.04.065.
  • Sasaki, S.; Kato, K.; Yoshifuji, M. Synthesis and Redox Properties of Crowded Triarylphosphines Carrying a Nitroxide Radical and Related Compounds. BCSJ. 2007, 80, 1791–1798. DOI: 10.1246/bcsj.80.1791.
  • Ohkubo, K.;Nanjo, T.;Fukuzumi, S. Photocatalytic Electron-Transfer Oxidation of Triphenylphosphine and Benzylamine with Molecular Oxygen via Formation of Radical Cations and Superoxide Ion. BCSJ. 2006, 79, 1489–1500. DOI: 10.1246/bcsj.79.1489.
  • Yasui, S.;Tojo, S.;Majima, T. Effects of Substituents on Aryl Groups during the Reaction of Triarylphosphine Radical Cation and Oxygen. Org. Biomol. Chem. 2006, 4, 2969–2973. DOI: 10.1039/b606857j.
  • Yasui, S.;Tsujimoto, M. Investigation of Non-Rehm-Weller Kinetics in the Electron Transfer from Trivalent Phosphorus Compounds to Singlet Excited Sensitizers. J. Phys. Org. Chem. 2013, 26, 1090–1097. DOI: 10.1002/poc.3170.
  • Bach, R.D.; Winter,J.E.; McDouall, J.J.W. Relative Nucleophilicity: The Role of Solvation and Thermodynamics. J. Am. Chem. Soc. 1995, 117, 8586–8593; DOI: 10.1021/ja00138a014.
  • Bach, R. D.;Glukhovtsev, M. N.;Canepa, C. Oxidation of Alkenes, Sulfides, Amines, and Phosphines with Peroxynitrous Acid:  Comparison with Other Oxidants Such as Peroxyformic Acid and Dimethyldioxirane. J. Am. Chem. Soc. 1998, 120, 775–783. DOI: 10.1021/ja972518h.
  • Ho, D.G.; Gao, R.; Celaje, J.; Chung, H.Y.; Selke, M. Phosphadioxirane: A Peroxide from an Ortho-Substituted Arylphosphine and Singlet Dioxygen. Science 2003, 302, 259–262. DOI: 10.1126/science.1089145.
  • Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Petersson, G.A.; Nakatsuji, H.; et al. Gaussian 16, Revision C.01, Gaussian, Inc.: Wallingford, CT, 2019.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.