Toward Hexaphenylethane: Structure and Decomposition of Crystalline Triphenylmethyl Iodide

Chemistry of Materials

Volumn 8, Issue 7, 1996, Pages 1500-1503

  Arkin, C Richard ^a   Cowans, Brett ^a   Kahr, Bart ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001514638     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm9600889     Document Type: Article

References (21)

1. Gomberg, M. Ber. Dtsch. Chem. Ges. 1900, 33, 3150; J. Am. Chem. Soc. 1900, 22, 757.
2. Gomberg, M. Ber. Dtsch. Chem. Ges. 1900, 33, 3150; J. Am. Chem. Soc. 1900, 22, 757.
3. 1
4. Triphenylmethyl chloride: Kahr, B.; Carter, R. L. Mol. Cryst. Liq. Cryst. 1992, 279, 79. Dunand, A.; Gerdil, R. Acta Crystallogr., Sect. B 1982, B38, 570; Triphenylmethyl bromide: Dunand, A.; Gerdil, R. Acta Crystallogr., Sect. B 1984, B40, 59. 1,1,1-Triphenylethane: Destro, R.; Pilati, T.; Simonetta, M. Acta Crystallogr., Sect. B 1980, B36, 2495.
5. Triphenylmethyl chloride: Kahr, B.; Carter, R. L. Mol. Cryst. Liq. Cryst. 1992, 279, 79. Dunand, A.; Gerdil, R. Acta Crystallogr., Sect. B 1982, B38, 570; Triphenylmethyl bromide: Dunand, A.; Gerdil, R. Acta Crystallogr., Sect. B 1984, B40, 59. 1,1,1-Triphenylethane: Destro, R.; Pilati, T.; Simonetta, M. Acta Crystallogr., Sect. B 1980, B36, 2495.
6. Triphenylmethyl chloride: Kahr, B.; Carter, R. L. Mol. Cryst. Liq. Cryst. 1992, 279, 79. Dunand, A.; Gerdil, R. Acta Crystallogr., Sect. B 1982, B38, 570; Triphenylmethyl bromide: Dunand, A.; Gerdil, R. Acta Crystallogr., Sect. B 1984, B40, 59. 1,1,1-Triphenylethane: Destro, R.; Pilati, T.; Simonetta, M. Acta Crystallogr., Sect. B 1980, B36, 2495.
7. Triphenylmethyl chloride: Kahr, B.; Carter, R. L. Mol. Cryst. Liq. Cryst. 1992, 279, 79. Dunand, A.; Gerdil, R. Acta Crystallogr., Sect. B 1982, B38, 570; Triphenylmethyl bromide: Dunand, A.; Gerdil, R. Acta Crystallogr., Sect. B 1984, B40, 59. 1,1,1-Triphenylethane: Destro, R.; Pilati, T.; Simonetta, M. Acta Crystallogr., Sect. B 1980, B36, 2495.
8. This is a common packing motif for triphenylmethyl-X derivatives. See examples in ref 3.
9. For a historical view of the triphenylmethyl equilibrium, see: McBride, J. M. Tetrahedron 1974, 30, 2009.
10. See, for example: Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433.
11. Yannoni, N.; Kahr, B.; Mislow, K. J. Am. Chem. Soc. 1988, 110, 6670. Kahr, B.; Van Engen, D.; Mislow, K. J. Am. Chem. Soc. 1986, 108, 8305.
12. Yannoni, N.; Kahr, B.; Mislow, K. J. Am. Chem. Soc. 1988, 110, 6670. Kahr, B.; Van Engen, D.; Mislow, K. J. Am. Chem. Soc. 1986, 108, 8305.
13. Our signal was identical with that from the triphenylmethyl radical of Janzen, obtained by γ-irradiation of crystalline triphenylmethyl carboxylates. Janzen, E. G.; Buchheit, M. J. Phys. Chem. 1972, 76, 937.
14. Pople, J. A. Mol. Phys. 1958, 1, 168.
15. Staab, H. A.; Brettschneider, H.; Brunner, H. Chem. Ber. 1970, 103, 1101.
16. Ullman, F.; Borsum, W. Ber. Dtsch. Chem. Ges. 1902, 35, 2877.
17. Kahr, B. Dissertation, Princeton University, 1988.
18. A similar result was obtained in the pyrolysis of triphenylmethyl acetate. See: Hurd, C. D.; Mold, J. D. J. Org. Chem. 1948, 13, 339.
19. Lewis, H. G.; Owen, E. D. J. Chem. Soc. B 1967, 422.
20. 2 pushes the photostationary state in the reverse direction, back toward the formation of 1.
21. Wood, K. V.; Bonham, C.; Hipskind, J.; Nicholson, R. L. Phytochemistry 1994, 37, 557.