Azophenolic Acerands: Amine-Selective Coloration and Crystal Structure of a Piperidinium Saltex

Journal of the American Chemical Society

Volumn 111, Issue 5, 1989, Pages 1881-1883

  Kaneda, Takahiro ^a   Umeda, Shin'ichi ^a   Ishizaki, Yuka ^a   Kuo, Hsien Saw ^a   Misumi, Soichi ^a   Kai, Yasushi ^a   Kanehisa, Nobuko ^a   Kasai, Nobutami ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845184855     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00187a054     Document Type: Article

References (9)

1. We have suggested the term “saltex” in place of “salt complex” in ref lk. For synthetic saltexes whose structures have been determined by X-ray crystallographic analysis: (a) Goldberg, I. Acta Crystallogr., Sect. B 1975, B31, 2592–2600. (b) Newcomb, M.; Moore, S. S.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6405–6410. (c) Behr, J. P.; Lehn, J. M.; Moras, D.; Thierry, J. C. J. Am. Chem. Soc. 1981, 103, 701–703. (d) Daly, J. J.; Schoenholzere, P.; Behr, J. P.; Lehn, J. M. Helv. Chem. Acta 1981, 64, 1444–1451. (e) Browne, C. M.; Ferguson, G.; McKervey, M. A.; Mulholland, D. L.; O'-Conner, T.; Parvez, M. J. Am. Chem. Soc. 1985, 107, 2703–2712. (f) Bradshaw, J. S.; Chamberlin, D. A.; Harrison, P. E.; Wilson, B. E.; Arena, G.; Dailey, N. K.; Lamb, J. D.; Izatt, R. M. J. Org. Chem. 1985, 50, 3065–3069. (g) Bradshaw, J. S.; Colter, M. L.; Nakatsuji, Y.; Spencer, N. O.; Brown, M. F.; Izatt, R. M.; Arena, G.; Tse, P.-K.; Wilson, B. E.; Lamb, J. D.; Dailey, N. K. J. Org. Chem. 1985, 50, 4865–4872. (h) Cheverier, B.; Moras, D.; Behr, J. P.; Lehn, J. M. Acta Crystallogr. 1987, C43, 2134–2137. (i) Bradshaw, J. S.; McDaniel, C. W.; Skidmore, B. D.; Nielsen, R. B.; Wilson, B. E.; Dailey, N. K.; Izatt, R. M. J. Heterocyclic Chem. 1987, 24, 1085–1092. (j) McMurry, T. J.; Hosseini, M. W.; Garrett, T. M.; Hahn, F. E.; Reyes, Z. E.; Raymond, K. N. J. Am. Chem. Soc. 1987, 109, 7196–7198. (k) Kaneda, T.; Ishizaki, Y.; Misumi, S.; Kai, Y.; Hirao, G.; Kasai, N. J. Am. Chem. Soc. 1988, 110, 2970–2972.
2. (a) Yamazaki, N.; Nakahama, S.; Hirao, A.; Negi, S. Tetrahedron Lett. 1978, 2429–2432. (b) Nakamura, H.; Sakka, H.; Takagi, M.; Ueno, K. Chem. Lett. 1981, 1305–1306. (c) Kaneda, T.; Sugihara, K.; Kamiya, H., Misumi, S. Tetrahedron Lett. 1981, 22, 4407–4408. (d) Sugihara, K.; Kaneda, T.; Misumi, S. Heterocycles 1982, 18, 57–61. (e) Hiratani, K. Chem. Lett. 1982, 1021–1024. (f) Tanigawa, I.; Tsuemoto, K.; Kaneda, T.; Misumi, S. Tetrahedron Lett. 1984, 25, 5327–5330. (g) Hiratani, K.; Taguchi, K.; Sugihara, H.; Ito, K. Bull. Chem. Soc. Jpn. 1984, 57, 1976–1984. (h) Kaneda, T.; Umeda, S.; Tanigawa, H.; Misumi, S.; Kai, Y.; Morii, H.; Miki, K.; Kasai, N. J. Am. Chem. Soc. 1985, 107, 4802–4803. (i) Bartsch, R. A.; Czech, B. P.; Kang, S. I.; Stewart, L. E.; Walkowiak, W.; Charewicz, W. A.; Heo, G. S.; Son, B. J. Am. Chem. Soc. 1985, 107, 4997–4998. (j) Kimura, K.; Sakamoto, H.; Kitazawa, S.; Shono, T. J. Chem. Soc., Chem. Commun. 1985, 669–670. (k) Hiratani, Bull. Chem. Soc. Jpn. 1985, 58, 420–423. (1) Hiratani, K.; Taguchi, K. Bull. Chem. Soc. Jpn. 1987, 60, 3827–3833. (m) Nakashima, K.; Nagaoka, Y.; Nakatsuji, S.; Kaneda, T.; Tanigawa, I.; Hirose, K.; Misumi, S.; Akiyama, S. Bull. Chem. Soc. Jpn. 1987, 60, 3219–3223. (n) For a review: Hiratani, K. J. Synth. Org. Chem., Jpn. 1987, 45, 1186–1198.
3. There have been considerable reports describing metal ion-selective coloration. (a) Cram, D. J.; Carmack, R. A.; Helgeson, R. C. J. Am. Chem. Soc. 1988, 110, 571–577. (b) van Gent, J.; Sudholter, E. J. R.; Lambeck, P. V.; Popma, T. J. A.; Gerritsma, G. J.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1988, 893–895. For reviews: (c) Takagi, M.; Ueno, K. Top. Curr. Chem. 1984, 121, 39–65. (d) Löhr, H.-G.; Vg¨tle, F. Acc. Chem. Res. 1985, 18, 65–72. (e) Takagi, M.; Nakamura, H. J. Coord. Chem. 1986, 15, 53–82. (f) Misumi, S.; Kaneda, T. Mem. Inst. Sci. Ind. Res., Osaka Univ. 1987, 44, 29–47. (g) Kaneda, T. J. Synth. Org. Chem., Jpn. 1988, 46, 96–107, and references cited therein.
4. (a) Glockner, B. Monatsh. Chem. 1949, 80, 493–498. (b) Juvvik, P.: Sundby, B. Acta Chem. Scand. 1978, 27, 1645–1652, 3632–3640.
5. Sheldrick, G. M. Crystallographic Computing 3; Sheldrick, G. M., Kruger, C., Goddard, R., Eds.; Oxford University Press: 1985; pp 175–189.
6. Stewart, J. M. XRAY-76: Report TR-446, University of Maryland, MD, 1976.
7. Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703–2707.
8. Izatt, R. M.; Izatt, N. E.; Rossiter, B. E.; Christensen, J. J.; Haymore, B. L. Science 1978, 199, 994–996.
9. Kaneda, T.; Hirose, K.; Misumi, S. J. Am. Chem. Soc., in press.