Isolation and X-ray Crystallographic Analysis of a Stable Selenenic Acid

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 20, 1997, Pages 2223-2224

  Saiki, Toshiyuki ^a   Goto, Kei ^a   Okazaki, Renji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Calixarenes; Selenium; Steric hindrance; Structure elucidation

Indexed keywords

EID: 0030668415     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199722231     Document Type: Article

References (40)

1. For reviews, see: a) The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1 and 2 (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1986, and 1987, respectively; b) Organoselenium Chemistry (Ed.: D. Liotta), Wiley, New York, 1987; c) P. D. Magnus in Comprehensive Organic Chemistry, Vol. 3 (Ed.: D. N. Jones), Pergamon, Oxford, 1979, pp. 491-538.
2. For reviews, see: a) The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1 and 2 (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1986, and 1987, respectively; b) Organoselenium Chemistry (Ed.: D. Liotta), Wiley, New York, 1987; c) P. D. Magnus in Comprehensive Organic Chemistry, Vol. 3 (Ed.: D. N. Jones), Pergamon, Oxford, 1979, pp. 491-538.
3. For reviews, see: a) The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1 and 2 (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1986, and 1987, respectively; b) Organoselenium Chemistry (Ed.: D. Liotta), Wiley, New York, 1987; c) P. D. Magnus in Comprehensive Organic Chemistry, Vol. 3 (Ed.: D. N. Jones), Pergamon, Oxford, 1979, pp. 491-538.
4. a) L. Flohé in Free Radicals in Biology, Vol. V. (Ed.: W. A. Pryor), Academic Press, New York, 1982, pp. 223-254;
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6. For recent examples, see: a) T. G. Back, B. P. Dyck, J. Am. Chem. Soc. 1997, 119, 2079-2083; b) L. Engman, C. Andersson, R. Morgenstern, I. A. Cotgreave, C. M. Andersson, A. Hallberg, Tetrahedron 1994, 50, 2929-2938; c) M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1994, 116, 2557-2561, and references therein.
7. For recent examples, see: a) T. G. Back, B. P. Dyck, J. Am. Chem. Soc. 1997, 119, 2079-2083; b) L. Engman, C. Andersson, R. Morgenstern, I. A. Cotgreave, C. M. Andersson, A. Hallberg, Tetrahedron 1994, 50, 2929-2938; c) M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1994, 116, 2557-2561, and references therein.
8. For recent examples, see: a) T. G. Back, B. P. Dyck, J. Am. Chem. Soc. 1997, 119, 2079-2083; b) L. Engman, C. Andersson, R. Morgenstern, I. A. Cotgreave, C. M. Andersson, A. Hallberg, Tetrahedron 1994, 50, 2929-2938; c) M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1994, 116, 2557-2561, and references therein.
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17. Although some of those relatively stable selenenic acids were claimed to be isolable [4,5c], reinvestigations of the structures of the isolated products revealed that they are not selenenic acids but the corresponding selenenic anhydrides: a) H. J. Reich, W. W. Willis, Jr., S. Wollowitz, Tetrahedron Lett. 1982, 23, 3319-3322; b) J. L. Kice, F. McAfee, H. Slebocka-Tilk, ibid. 1982, 23, 3323-3326.
18. Although some of those relatively stable selenenic acids were claimed to be isolable [4,5c], reinvestigations of the structures of the isolated products revealed that they are not selenenic acids but the corresponding selenenic anhydrides: a) H. J. Reich, W. W. Willis, Jr., S. Wollowitz, Tetrahedron Lett. 1982, 23, 3319-3322; b) J. L. Kice, F. McAfee, H. Slebocka-Tilk, ibid. 1982, 23, 3323-3326.
19. H. J. Reich, C. P. Jasperse, J. Org. Chem. 1988, 53, 2389-2390.
20. Possible exceptions are anthraquinoneselenenic acids [5a,b], whose structural determination was based only on elemental analysis and UV/Vis spectra.
21. a) N. Tokitoh, T. Saiki, R. Okazaki, J. Chem. Soc. Chem. Commun. 1995, 1899-1900;
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24. d) T. Saiki, K. Goto, R. Okazaki, Chem. Lett. 1996, 993-994. For related compounds, see:
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26. e) K. Goto, N. Tokitoh, R. Okazaki, Angew. Chem. 1995, 107, 1202-1203; Angew. Chem. Int. Ed. Engl. 1995, 34, 1124-1126:
27. f) K. Goto, M. Holler, R. Okazaki, J. Am. Chem. Soc. 1997, 119, 1460-1461.
28. Recently, the bridged calix[6]arenes containing a functional group on the bridge were also described by Lüning et al. a) H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723-2725; Angew. Chem., Int. Ed. Engl. 1995, 34, 2555-2557; b) Liebigs Ann. 1996, 1367-1373; c) Tetrahedron 1996, 52, 10879-10882.
29. Recently, the bridged calix[6]arenes containing a functional group on the bridge were also described by Lüning et al. a) H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723-2725; Angew. Chem., Int. Ed. Engl. 1995, 34, 2555-2557; b) Liebigs Ann. 1996, 1367-1373; c) Tetrahedron 1996, 52, 10879-10882.
30. Recently, the bridged calix[6]arenes containing a functional group on the bridge were also described by Lüning et al. a) H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723-2725; Angew. Chem., Int. Ed. Engl. 1995, 34, 2555-2557; b) Liebigs Ann. 1996, 1367-1373; c) Tetrahedron 1996, 52, 10879-10882.
31. Recently, the bridged calix[6]arenes containing a functional group on the bridge were also described by Lüning et al. a) H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723-2725; Angew. Chem., Int. Ed. Engl. 1995, 34, 2555-2557; b) Liebigs Ann. 1996, 1367-1373; c) Tetrahedron 1996, 52, 10879-10882.
32. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100401. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: int. code +(1223) 336-033; e-mail: deposit@chemcrys.cam.ac.uk).
33. J. H. Bryden, J. D. McCullough, Acta Crystallogr. 1954, 7, 833-838.
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36. The intramolecular interaction between a divalent selenium and an amino group has been studied in detail: a) M. Iwaoka, S. Tomoda, Phosphorus Sulfur Silicon Relat. Elem. 1992, 67, 125-130; b) J. Am. Chem. Soc. 1996, 118, 8077-8084. Also see ref. [3c].
37. The intramolecular interaction between a divalent selenium and an amino group has been studied in detail: a) M. Iwaoka, S. Tomoda, Phosphorus Sulfur Silicon Relat. Elem. 1992, 67, 125-130; b) J. Am. Chem. Soc. 1996, 118, 8077-8084. Also see ref. [3c].
38. N. Walker, D. Stuart, Acta Crystallogr. Sect. A 1983, 39, 158-166.
39. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits, C. Smykalla, The DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1992.
40. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, R. de Gelder, R. Israel, J. M. M. Smits, The DIRDIF-94 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1994.