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References
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- Kobayashi, J.; Goto, K.; Kawashima, T.; Schmidt, M. W.; Nagase, S. Synthesis, Structure, and Bonding Properties of 5-Carbaphosphatranes: A New Class of Main Group Atrane. J. Am. Chem. Soc. 2002, 124, 3703–3712. DOI: 10.1021/ja011458j.
- Nakafuji, S.-y.; Kobayashi, J.; Kawashima, T.; Schmidt, M. W. Solvent-Dependent Crystallization of 1-Hydro-6-Carbaphosphatrane and Its Tautomer. Inorg. Chem. 2005, 44, 6500–6502. DOI: 10.1021/ic050679d.
- Kobayashi, J.; Kawashima, T, For anti-apicophilic phosphorus compounds. Chemistry of Pentacoordinate anti-Apicophilic Phosphorus Compounds. CR. Chim. 2010, 13, 1249–1259. DOI: 10.1016/j.crci.2010.06.010.
- For phosphine oxides see: Horner, L.; Balzer, W. D. Phosphororganische verbindungen IXL zum sterischen verlauf der desoxygenierung von tertiären phosphinoxyden zu tertiären phosphinen mit trichlorsilan. Tetrahedron Lett. 1965, 6, 1157–1162. DOI: 10.1016/S0040-4039(01)83990-3.; Naumann, K.; Zon, G.; Mislow, K. The Use of Hexachlorodisilane as a Reducing Agent. Stereospecific Deoxygenation of Acyclic Phosphine Oxides. J. Am. Chem. Soc. 1969, 91, 7012–7023. 10.1021/ja01053a021. For phosphine sulfides, see: Zon, K.; DeBruin K. E.; Naumann, K.; Mislow, K. The Stereospecific Desulfurization of Acyclic Phosphine Sulfides with Hexachlorodisilane and the Alkaline Hydrolysis of Monoalkoxy- and Monoalkyl- mercaptophosphonium Salts. Stereochemistry and Mechanism. J. Am. Chem. Soc. 1969, 91, 7023–7027. 10.1021/ja011458j.
- Compound 8b was determined to have the structure as shown in Scheme 2 by X-ray crystallographic analysis (see Supplemental Materials). The plausible formation mechanism of 8a having a cationic part as same as that of 8b is shown in Supplemental Materials.
- Hellwinkel, D. Wasserstoffderivate, Radikale Und Anionen Des Fünfbindigen Phosphors. Chem. Ber. 1969, 102, 528–547. DOI: 10.1002/cber.19691020220.
- Akiba, K.-y.; Okada, K.; Ohkata, K. Formation of Ammoniophosphoranes by Transannular Interaction in Dibenz[c,f][1,5]Azaphosphocine System. Tetrahedron Lett. 1986, 27, 5221–5224. DOI: 10.1016/S0040-4039(00)85174-6.
- We should not negrect the exisence of an interaction between phosphorus center and p-fluorine atom of one of the pentafluorophenyl groups on the boron as shown by the fact that the distance (2.029 Å) of P···F is shorter than the sum (3.27 Å) of van der Waals radii of P and F. However, this interaction seems not strong enough for 8b to have a trigonal pyramidal structure.
- Yamamoto, A.; Satoh, W.; Yamamoto, Y.; Akiba, K.-y., Conversion reaction from P-Cl bond to P-Me bond, see: Phosphorus Octaethyltetraphenylporphyrins [(Oetpp)P(Me)(X)]PF6 (X = Me, OH, F) Having Saddle (X = Me) or Ruffled (X = OH, F) Conformations. Chem. Commun. 1999, 35, 147–148. DOI: 10.1039/a809601e.
- Homocubyl system, see: Turnblom, E. W.; Katz, T. J. Stable pentaakylphos- phorane. J. Am. Chem. Soc. 1971, 93, 4065–4066. DOI: 10.1021/ja00745a051. Turnblom, E. W.; Katz, T. J. Synthesis of alkylphosphoranes. J. Am. Chem. Soc. 1973, 95, 4292–4311. 10.1021/ja00794a027, Spirocyclic system, see: Schmidbaur, H.; Holl, P.; Köhler, F. H. 5-Methyl-5 λ5-phosphaspiro [4.4] nonane—The Simplest Pentaalkylphosphorane Yet Obtained. Angew. Chem. Int. Ed. 1977, 16, 722. 10.1002/anie.197707221. Monkowius, U.; Mitzel, N. W.; Schier, A.; Schmidbaur, H. 5-Organyl-5-phosphaspiro[4.4]nonanes: A Contribution to the Structural Chemistry of Spirocyclic Tetraakylphosphonium Salts and Pentaalkyl- phosphoranes. J. Am. Chem. Soc. 2002, 124, 6126–6132. 10.1021/ja012041g.