On Attempts at Generation of Carboranyl Carbocation

Journal of Organic Chemistry

Volumn 68, Issue 25, 2003, Pages 9589-9597

  Tsuji, Motonori ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b 202 Kinoshita coop ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; DECOMPOSITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; SYNTHESIS (CHEMICAL);

DIAZOTIZATION; SUPERACIDS;

ISOMERS;

CARBORANE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0344235373     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035090f     Document Type: Article

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69. Gleiter, R.; Hoffmann, R.; Stohrer, W.-D. Chem. Ber. 1972, 105, 8-23. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696-701. Dill, J. D.; Schleyer, P. v. R.; Binkley, J. S.; Seeger, R.; Pople, J. A.; Haselbach, E. J. Am. Chem. Soc. 1976, 98, 5428-5431.
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72. Fort, R. C., Jr.; Schleyer, P. v. R. J. Am. Chem. Soc. 1964, 86, 4194-4195. Schleyer, P. v. R.; Fort, R. C., Jr.; Watts, W. E.; Comisarow, M. B. ; Olah, G. A. J. Am. Chem. Soc. 1964, 86, 4195-4197. Müller, P.; Mareda, J. Helv. Chim. Acta 1987, 70, 1017-1024.
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76. Tanida, H.; Tsuji, T.; Irie, T. J. Am. Chem. Soc. 1967, 89, 1953-1954. Battiste, M. A.; Deyrup, C. L.; Pincock, R. E.; Haywood-Farmer, J. J. Am. Chem. Soc. 1967, 89, 1954-1955. Olah, G. A.; Liang, G.; Mateescu, G. D.; Riemenshneider, J. L. J. Am. Chem. Soc. 1973, 95, 8698-8702. Masamune, S.; Sakai, M.; Kemp-Jones, A. V. Can. J. Chem. 1974, 52, 858-860. Laube, T. J. Am. Chem. Soc. 1989, 111, 9224-9232. Winstein, S. Quart. Rev. 1969, 23, 141-176.
77. Tanida, H.; Tsuji, T.; Irie, T. J. Am. Chem. Soc. 1967, 89, 1953-1954. Battiste, M. A.; Deyrup, C. L.; Pincock, R. E.; Haywood-Farmer, J. J. Am. Chem. Soc. 1967, 89, 1954-1955. Olah, G. A.; Liang, G.; Mateescu, G. D.; Riemenshneider, J. L. J. Am. Chem. Soc. 1973, 95, 8698-8702. Masamune, S.; Sakai, M.; Kemp-Jones, A. V. Can. J. Chem. 1974, 52, 858-860. Laube, T. J. Am. Chem. Soc. 1989, 111, 9224-9232. Winstein, S. Quart. Rev. 1969, 23, 141-176.
78. Tanida, H.; Tsuji, T.; Irie, T. J. Am. Chem. Soc. 1967, 89, 1953-1954. Battiste, M. A.; Deyrup, C. L.; Pincock, R. E.; Haywood-Farmer, J. J. Am. Chem. Soc. 1967, 89, 1954-1955. Olah, G. A.; Liang, G.; Mateescu, G. D.; Riemenshneider, J. L. J. Am. Chem. Soc. 1973, 95, 8698-8702. Masamune, S.; Sakai, M.; Kemp-Jones, A. V. Can. J. Chem. 1974, 52, 858-860. Laube, T. J. Am. Chem. Soc. 1989, 111, 9224-9232. Winstein, S. Quart. Rev. 1969, 23, 141-176.
79. Haywood-Farmer, J. Chem. Rev. 1974, 74, 315-350.
80. We conducted a preliminary investigation of the hydride affinities of carboranyl carbocations. The B3LYP/6-31G* method shows that the three topological carboranyl carbocations are more unstable than the phenyl cation (relative energy differences: 22 kcal/mol for 12a, 19 kcal/mol for 12b, 16 kcal/mol for 12c).
81. Aschi, M.; Harvey, J. N. J. Chem. Soc., Perkin Trans. 2 1999, 1059-1062.
82. Subramanian, L. R.; Hanack, M.; Chang, L. W. K.; Imhoff, M. A.; Schleyer, P. v. R.; Effenberger, F.; Kurtz, W.; Stang, P. J.; Dueber, T. E. J. Org. Chem. 1976, 41, 4099-4103. Streitwieser, A., Jr.; Dafforn, A. Tetrahedron Lett. 1976, 1435-1438.
83. Subramanian, L. R.; Hanack, M.; Chang, L. W. K.; Imhoff, M. A.; Schleyer, P. v. R.; Effenberger, F.; Kurtz, W.; Stang, P. J.; Dueber, T. E. J. Org. Chem. 1976, 41, 4099-4103. Streitwieser, A., Jr.; Dafforn, A. Tetrahedron Lett. 1976, 1435-1438.
84. Himeshima, Y.; Kobayashi, H.; Sonoda, T. J. Am. Chem. Soc. 1985, 107, 5286-5288.
85. Cheng, T.-Y.; Bullock, R. M. J. Am. Chem. Soc. 1999, 121, 3150-3155.
86. Schoberth, W.; Hanack, M. Synthesis 1972, 703.
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88. In the case of the phenyl cation, the bond shortening between the cation center and the adjacent carbon atoms has been predicted (1.33, Å for 15a and 1.40, Å for benzene at the B3LYP/6-31G* level, respectively). See also ref 32. Similarly, the shortening of the C-C distance of o-carboranyl carbocation 12a (1.59 A) can be predicted at the B3LYP/6-31G* level, as compared with the parent 1a (1.63 Å). In the case of carboranes, however, it seems that the abnormally long C-C distance, as well as its high degree of instability (ref 36), is not advantageous for stabilization by means of either of either homoconjugative or hyperconjugative substituents.
89. Zollinger, H. Acc. Chem. Res. 1973, 6, 335-341.
90. The syntheses of C′-unsubstituted C-hydroxy-o-carborane derivatives, i.e., acetate (6a), tosylate (7a), and triflate (8a), required precisely one equivalent of pyridine; however, the syntheses in the case of both m- and p-carboranes were carried out in an excess of pyridine.