Charge–transfer excitation of electron donor–acceptor complexes of arylcyclopropanes

Abstract

Electron-transfer (ET) reactions of mono- and di-arylcyclopropanes 1 and 2 have been investigated by employing charge-transfer (CT) excitation of their electron donor–acceptor (EDA) complexes with tetracyanoethylene (TCNE) or p-chloranil (CA). For the TCNE complexes, no reaction is observed following photoexcitation within their CT bands. Picosecond absorption spectroscopic experiments with phenylcyclopropane 1a and 1,1-diphenylcyclopropane 2a reveal that the photogenerated ion radical pairs [1a˙⁺, TCNE˙^-] and [2a˙⁺, TCNE˙^-] are too short-lived to undergo chemical reaction. For the CA complexes, net chemical change is observed in the CT excitation of the 2a–CA complex though the efficiency is very low. The other arylcyclopropane–CA complexes are found to be unreactive. Factors concerned with the reactivity of 1 and 2 upon their CT-excitation are discussed.

References

1. H. D. Roth, Acc. Chem. Res., 1987, 20, 343; P. G. Gassman, Photoinduced Electron Transfer, Part C, eds. M. A. Fox and M. Chanon, Elsevier, Amsterdam, 1988, p. 70; H. D. Roth, Top. Curr. Chem., 1992, 163, 131.
2. E. Haselbach, Chem. Phys. Lett., 1970, 7, 428; C. G. Rowland, Chem. Phys. Lett., 1971, 9, 169; J. R. Collins and G. A. Gallup, J. Am. Chem. Soc., 1982, 104, 1530; D. D. M. Wayner, R. J. Boyd and D. R. Arnold, Can. J. Chem., 1983, 61, 2310; 1985, 63, 3283; P. Du, D. A. Hrovat and W. T. Borden, J. Am. Chem. Soc., 1988, 110, 3405; S. S. Shaik and J. P. Dinnocenzo, J. Org. Chem., 1990, 55, 3434; L. A. Eriksson and S. Lunell, J. Am. Chem. Soc., 1992, 114, 4532; K. Krogh-Jespersen and H. D. Roth, J. Am. Chem. Soc., 1992, 114, 8388; C. E. Hudson, C. S. Giam and D. J. McAdoo, J. Org. Chem., 1993, 58, 2017; S. Shaik, A. C. Reddy, A. Ioffe, J. P. Dinnocenzo, D. Danovich and J. K. Cho, J. Am. Chem. Soc., 1995, 117, 3205.
3. Photoelectron spectroscopy: H. Basch, M. B. Robin, N. A. Kuebler, C. Baker and D. W. Turner, J. Chem. Phys., 1969, 51, 52; G. Bieri, F. Burger, E. Heilbronner and J. P. Maier, Helv. Chim. Acta., 1977, 60, 2213.
4. Gas phase reactivity: L. W. Sieck, R. Gorden, Jr. and P. Ausloos, J. Am. Chem. Soc., 1972, 94, 7157; P. N. T. Van Velzen and W. Van der Hart, J. Chem. Phys., 1981, 61, 335; S. G. Lias and T. J. Buckley, Int. J. Mass Spectrum. Ion Processes, 1984, 56, 123; T. M. Sack, D. L. Miller and M. L. Gross, J. Am. Chem. Soc., 1985, 107, 6795.
5. CIDNP: H. D. Roth and M. L. M. Schilling, J. Am. Chem. Soc., 1980, 102, 7956; H. D. Roth and M. L. M. Schilling, Can. J. Chem., 1983, 61, 1027; H. D. Roth and M. L. M. Schilling, J. Am. Chem. Soc., 1983, 105, 6805; C. J. Abelt, H. D. Roth and M. L. M. Schilling, J. Am. Chem. Soc., 1985, 107, 4148; H. D. Roth, M. L. M. Schilling and F. C. Schilling, J. Am. Chem. Soc., 1985, 107, 4152.
6. EPR studies: M. Iwasaki, K. Toriyama and K. Nunome, J. Chem. Soc., Chem. Commun., 1983, 202; X.-Z. Qin, L. D. Snow and F. Williams, J. Am. Chem. Soc., 1984, 106, 7640; M. Iwasaki, K. Toriyama and K. Nunome, Faraday Discuss. Chem. Soc., 1984, 78, 19; S. Lunell, M. B. Huang and A. Lund, Faraday Discuss. Chem. Soc., 1984, 78, 35; X.-Z. Qin and F. Williams, Tetrahedron, 1986, 42, 6301.
7. Vinylcyclopropanes: (a) J. P. Dinnocenzo and M. Schmittel, J. Am. Chem. Soc., 1987, 109, 1561; (b) J. P. Dinnocenzo and D. A. Conlon, J. Am. Chem. Soc., 1988, 110, 2324; (c) H. D. Roth and T. Herbertz, J. Am. Chem. Soc., 1993, 115, 9804; (d) H. Weng, V. Sethuraman and H. D. Roth, J. Am. Chem. Soc., 1994, 116, 7021; (e) H. Weng, Q. Sheik and H. D. Roth, J. Am. Chem. Soc., 1995, 117, 10655.
8. Bicyclo[1.1.0]butanes: P. G. Gassman, K. D. Olson, L. Walter and R. Yamaguchi, J. Am. Chem. Soc., 1981, 103, 4977; P. G. Gassman and K. D. Olson, J. Am. Chem. Soc., 1982, 104, 3740; H. D. Roth, M. L. M. Schilling, P. G. Gassman and J. L. Smith, J. Am. Chem. Soc., 1984, 106, 2711; P. G. Gassman and B. A. Hay, J. Am. Chem. Soc., 1985, 107, 4075; P. G. Gassman and B. A. Hay, J. Am. Chem. Soc., 1986, 108, 4227; A. Arnold and F. Gerson, J. Am. Chem. Soc., 1991, 113, 4359; A. Arnold, U. Burger, F. Gerson, E. Kloster-Jensen and S. P. Schmidlin, J. Am. Chem. Soc., 1993, 115, 4271.
9. Bicyclo[2.1.0]pentanes: W. Adam, H. Walter, G.-F. Chen and F. Williams, J. Am. Chem. Soc., 1992, 114, 3007; W. Adam, C. Sahin, J. Sendelbach, H. Walter, G.-F. Chen and F. Williams, J. Am. Chem. Soc., 1994, 116, 2576.
10. Spiropentanes: K. Ushida, T. Shida and J. C. Walton, J. Am. Chem. Soc., 1986, 108, 2805; Y. Takahashi, H. Ohaku, S. Morishima, T. Suzuki and T. Miyashi, Tetrahedron Lett., 1995, 36, 5207; Y. Takahashi, H. Ohaku, S. Morishima, T. Suzuki, H. Ikeda and T. Miyashi, J. Chem. Soc., Perkin Trans. 1, 1996, 319.
11. Methylenecyclopropanes: Y. Takahashi, T. Miyashi and T. Mukai, J. Am. Chem. Soc., 1983, 105, 6511; Y. Takahashi, T. Miyashi, T. Mukai, H. D. Roth and M. L. M. Schilling, J. Am. Chem. Soc., 1985, 107, 1079; T. Miyashi, M. Kamata and T. Mukai, J. Am. Chem. Soc., 1986, 108, 2755; J. Am. Chem. Soc., 1987, 109, 2780.
12. S. S. Hixson, J. Boyer and C. Gallucci, J. Chem. Soc., Chem. Commun., 1974, 540; P. C. Wong and D. R. Arnold, Tetrahedron Lett., 1979, 2101; D. R. Arnold and R. W. R. Humphreys, J. Am. Chem. Soc., 1979, 101, 2743; D. D. M. Wayner and D. R. Arnold, Can. J. Chem., 1985, 63, 871.
13. (a) P. H. Mazzocchi, C. Somich, M. Edwards, T. Morgan and H. L. Ammon, J. Am. Chem. Soc., 1986, 108, 6828; (b) H. Tomioka, D. Kobayashi, A. Hashimoto and S. Murata, Tetrahedron Lett., 1989, 30, 4685; (c) K. Maruyama, H. Imahori and Y. Ozawa, Chem. Lett., 1989, 2117; (d) C. Somich, P. H. Mazzocchi, M. Edwards, T. Morgan and H. L. Ammon, J. Org. Chem., 1990, 55, 2624; (e) Y. Takahashi, F. Endoh, H. Ohaku, K. Wakamatsu and T. Miyashi, J. Chem. Soc., Chem. Commun., 1994, 1127.
14. A. P. Schaap, L. Lopez, S. D. Anderson and S. D. Gagnon, Tetrahedron Lett., 1982, 23, 5493; K. Mizuno, N. Kamiyama, N. Ichinose and Y. Otsuji, Tetrahedron, 1985, 41, 2207; S. C. Shim and J. S. Song, J. Org. Chem., 1986, 51, 2817; N. Ichinose, K. Mizuno, T. Tamai and Y. Otsuji, J. Org. Chem., 1990, 55, 4079; K. Gollnick, X.-L. Xiao and U. Paulmann, J. Org. Chem., 1990, 55, 5945; K. Gollnick and U. Paulmann, J. Org. Chem., 1990, 55, 5954.
15. (a) V. R. Rao and S. S. Hixson, J. Am. Chem. Soc., 1979, 101, 6458; (b) K. Mizuno, J. Ogawa, H. Kagano and Y. Otsuji, Chem. Lett., 1981, 437; (c) K. Mizuno, J. Ogawa and Y. Otsuji, Chem. Lett., 1981, 741; (d) K. Mizuno, K. Yoshioka and Y. Otsuji, Chem. Lett., 1983, 941; (e) S. S. Hixson and Y. Xing, Tetrahedron Lett., 1991, 32, 173; (f) J. P. Dinnocenzo, W. P. Todd, T. R. Simpson and I. R. Gould, J. Am. Chem. Soc., 1990, 112, 2462; (g) J. P. Dinnocenzo, D. R. Lieberman and T. R. Simpson, J. Am. Chem. Soc., 1993, 115, 366.
16. S. L. Mattes and S. Farid, Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1983, vol. 6, p. 233; G. J. Kavarnos and N. J. Turro, Chem. Rev., 1986, 86, 401; J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825; M. A. Fox, Adv. Photochem., 1986, 13, 237; P. S. Mariano and J. L. Stavinoha, Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum, New York, 1984, p. 145; J. J. Maccullough, Chem. Rev., 1987, 87, 811; F. Müller and J. Mattay, Chem. Rev., 1993, 93, 99.
17. P. G. Gassman, K. T. Mansfield and T. J. Murphey, J. Am. Chem. Soc., 1969, 91, 1684; A. B. Evnin and D. R. Arnold, J. Am. Chem. Soc., 1968, 90, 5330; P. G. Gassman and G. D. Richmond, J. Am. Chem. Soc., 1970, 92, 2090.
18. (a) T. Martini and J. A. Kampmeier, Angew. Chem., Int. Ed. Engl., 1970, 9, 236; (b) R. Noyori, N. Hayashi and M. Kato, J. Am. Chem. Soc., 1971, 93, 4948; (c) P. G. Wiering, J. W. Verhoeven and H. Steinberg, J. Am. Chem. Soc., 1981, 103, 7675; (d) P. G. Wiering and H. Steinberg, J. Org. Chem., 1981, 46, 1663.
19. S. Nishida, I. Moritani and T. Teraji, J. Chem. Soc., Chem. Commun., 1971, 36; T. Tsuji and S. Nishida, Acc. Chem. Res., 1984, 17, 56; S. Nishida, M. Murakami, H. Oda, T. Tsuji, T. Mizuno, M. Matsubara and N. Kikai, J. Org. Chem., 1989, 54, 3859; S. Nishida, M. Murakami, T. Mizuno and T. Tsuji, J. Org. Chem., 1989, 54, 3868.
20. R. S. Mulliken and W. B. Pearson, Molecular Complexes: A Lecture and Reprint Volume, Wiley, New York, 1969; R. Foster, Organic Charge-Transfer Complexes, Academic Press, New York, 1969; G. Jones, II, Photoinduced Electron Transfer, Part A, eds. M. A. Fox and M. Chanon, Elsevier, Amsterdam, 1988, p. 245.
21. (a) E. F. Hilinski, J. M. Masnovi, C. Amatore, J. K. Kochi and P. M. Rentzepis, J. Am. Chem. Soc., 1983, 105, 6167; (b) E. F. Hilinski, J. M. Masnovi, J. K. Kochi and P. M. Rentzepis, J. Am. Chem. Soc., 1984, 106, 8071; (c) I. R. Gould, R. Moody and S. Farid, J. Am. Chem. Soc., 1988, 110, 7242; (d) I. R. Gould, R. H. Young, R. E. Moody and S. Farid, J. Phys. Chem., 1991, 95, 2068; (e) T. Asahi and N. Mataga, J. Phys. Chem., 1991, 95, 1956 See also refs. cited therein.
22. (a) T. Kobayashi and S. Nagakura, Chem. Lett., 1792, 903; (b) T. Kobayashi and S. Nagakura, Bull. Chem. Soc. Jpn., 1974, 47, 2563; (c) K. Watanabe, T. Nakayama and J. Mottl, J. Quant. Spectrosc. Radiat. Transfer, 1962, 2, 369; (d) K. Watanabe, J. Chem. Phys., 1957, 26, 542; (e) T. Koenig, M. Tuttle and R. A. Wielesek, Tetrahedron Lett., 1974, 2537; (f) E. Heilbronner, V. Hornung, F. H. Pinkerton and S. F. Thames, Helv. Chim. Acta, 1972, 55, 289.
23. (a) I. Prins, J. W. Verhoeven, T. J. deBoer and C. Worrell, Tetrahedron, 1977, 33, 127; (b) P. Bruckmann and M. Klessinger, Chem. Ber., 1974, 107, 1108; (c) K. Shudo, T. Kobayashi and C. Utsunomiya, Tetrahedron, 1977, 33, 1721.
24. Y. Takahashi, N. Nishioka, F. Endoh, H. Ikeda and T. Miyashi, Tetrahedron Lett., 1996, 37, 1841; Y. Takahashi, N. Nishioka, H. Ikeda and T. Miyashi, unpublished results.
25. L. Andrews, J. A. Harvey, B. J. Kelsall and D. C. Duffey, J. Am. Chem. Soc., 1981, 103, 6415.
26. N. C. Deno, H. G. Richey, J. S. Liu, D. N. Lincoln and J. O. Turner, J. Am. Chem. Soc., 1965, 87, 4533; C. F. Wilcox, L. M. Loew and R. Hoffman, J. Am. Chem. Soc., 1973, 95, 8192.
27. N. D. Bhaya and M. Shanshal, Z. Naturforsch, Teil A, 1980, 35, 137; W. J. E. Parr and T. Schaefer, J. Am. Chem. Soc., 1977, 99, 1033.
28. (a) R. C. Hahn, T. C. Corbin and H. Schechter, J. Am. Chem. Soc., 1968, 90, 3404; (b) R. C. Hahn, P. H. Howard, S.-M. Kong, G. A. Lorenzo and N. L. Miller, J. Am. Chem. Soc., 1969, 91, 3558; (c) R. C. Hahn, P. H. Howard and G. A. Lorenzo, J. Am. Chem. Soc., 1971, 93, 5816.
29. P. Bischof, R. Gleiter, E. Heilbronner, V. Hornung and G. Schröder, Helv. Chim. Acta., 1970, 53, 1645; R. Gleiter, E. Heilbronner and A. de Meijere, Helv. Chim. Acta., 1971, 54, 1029; E. Heilbronner, R. Gleiter, T. Hoshi and A. de Meijere, Helv. Chim. Acta, 1973, 56, 1594.
30. N. A. Clinton, R. S. Brown and T. G. Traylor, J. Am. Chem. Soc., 1970, 92, 5228; T. G. Traylor, W. Hatein, H. J. Berwin, N. A. Clinton and R. S. Brown, J. Am. Chem. Soc., 1971, 93, 5715; R. S. Brown and T. G. Traylor, J. Am. Chem. Soc., 1973, 95, 8025; D. F. Eaton and T. G. Traylor, J. Am. Chem. Soc., 1974, 96, 1226.
31. W. L. Jorgensen and L. Salem, The Organic Chemist's Book of Orbitals, Academic, New York, 1973, p. 23 and 154.
32. A. D. Walsh, Nature, 1947, 159, 165; A. D. Walsh, Trans. Faraday Soc., 1949, 45, 179; R. J. Buenker and S. D. Peyerimhoff, J. Phys. Chem., 1969, 73, 1299; R. Gleiter, Top. Curr. Chem., 1980, 86, 197.
33. L. T. Scott, I. Erden, W. R. Brunsvold, T. H. Schultz, K. N. Houk and M. N. Paddon-Row, J. Am. Chem. Soc., 1982, 104, 3659.
34. (a) Ketcham, R. Cavestri and D. Jambotkar, J. Org. Chem., 1963, 28, 2139; (b) R. E. Dunkelblum and B. Singer, Synthesis, 1975, 323; (c) A. Sanders and W. P. Giering, J. Org. Chem., 1973, 38, 3055.
35. J. A. Schmidt and E. F. Hilinski, Rev. Sci. Instrum., 1989, 60, 2902.