Synthesis, properties, oxidation, and electrochemistry of 1,2- dichalcogenins

Journal of the American Chemical Society

Volumn 122, Issue 21, 2000, Pages 5052-5064

  Block, Eric ^a   Birringer, Marc ^a   Deorazio, Russell ^a   Fabian, Jürgen ^d   Glass, Richard S ^b   Guo, Chuangxing ^a   He, Chunhong ^a   Lorance, Edward ^b   Qian, Quangsheng ^c   Schroeder, T Benjamin ^b   Shan, Zhixing ^a   Thiruvazhi, Mohan ^a   Wilson, George S ^c   Zhang, Xing ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

^c UNIVERSITY OF KANSAS   (United States)

^d DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICHALCOGENIN; THIARUBRINE A; THIOCYANIC ACID DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ELECTROCHEMISTRY; GEOMETRY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034737991     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994134s     Document Type: Article

References (123)

1. (a) Mortensen, J. T.; Sørensen, J. S.; Sørensen, N. A. Acta Chem. Scand. 1964, 18, 2392-2394.
2. (b) Bohlmann, F.; Kleine, K.-M. Chem. Ber. 1965, 98, 3081-3086.
3. (a) Norton, R. A.; Finlayson, A. J.; Towers, G. H. N. Phytochemistry 1985, 24, 356-357.
4. (b) Rodriguez, E. In Biologically Active Natural Products; Cutler, H. G., Ed.; ACS Symposium Series 380; American Chemical Society: Washington, DC, 1988; pp 432-437.
5. (c) Ellis, S. M.; Balza, F.; Constabel, J. B.; Towers, G. H. N. In Light-Activated Pest Control; ACS Symposium Series 616; American Chemical Society: Washington, DC, 1995; pp 165-178.
6. (d) Page, J. E.; Huffman, M. A.; Smith, V.; Towers, G. H. N. J. Chem. Ecol. 1997, 23, 2211-2226.
7. (e) Guillet, G.; Philogene, B. J. R.; O'Meara, J.; Durst, T.; Arnason, J. T. Phytochemistry 1997, 46, 495-498.
8. (f) De Viala, S. S.; Brodi, B. B.; Rodriguez, E.; Gibson, D. M. J. Nematol. 1998, 30, 192-200 and references therein.
9. (a) Viola, H.; Winkler, R. Methoden Organische Chemie; Houben-Weyl: 4th ed.; 1952; Vol. E9a, pp 209-249.
10. (b) Schroth, W.; Hintzsche, E.; Jordan, H.; Jende, T.; Spitzner, R.; Thondorf, I. Tetrahedron 1997, 53, 7509-7528.
11. (c) Huisgen, R.; Kalwinsh, I.; Moran, J. R.; Nöth, H.; Rapp, J. Liebigs Ann./Recl. 1997, 1677-1684.
12. (d) Schroth, W.; Spitzner, R.; Bruhn, C. Eur. J. Org. Chem. 1998, 2365-71.
13. (e) Wang, Y.; Koreeda, M.; Chatterji, T.; Gates, K. S. J. Org. Chem. 1998, 63, 8644-5.
14. (f) Block, E. Phosphorus Sulfur Relat. Elements 1999, 153/154, 173-192 and references therein.
15. (a) Cimiraglia, R.; Fabian, J.; Hess, B. A., Jr. J. Mol. Struct. (THEOCHEM) 1991, 230, 287-293.
16. (b) Schroth, W.; Jordan, H.; Spitzner, R. Tetrahedron Lett. 1995, 36, 1421-1424.
17. (c) Mann, M.; Fabian, J. J. Mol. Struct. (THEOCHEM) 1995, 331, 51-61.
18. (d) Pitchko, V.; Goddard, J. D. Chem. Phys. Lett. 1998, 289, 391-395.
19. (e) Ishida, T.; Oe, S.; Aihara, J. J. Mol. Struct. (THEOCHEM) 1999, 461-2, 553-559.
20. (f) Aihara, J.; Ishida, T. Bull. Chem. Soc. Jpn. 1999, 72, 937-941.
21. (g) Fabian, J.; Mann, M.; Petiau, M. J. Mol. Model. 2000, 6, 177-185.
22. (a) Schroth, W.; Billig, F.; Reinhold: C. Angew. Chem., Int. Ed. Engl. 1967, 6, 698-699.
23. (b) Schroth, W.; Billig F.; Languth, H. Z. Chem. 1965, 5, 353-354.
24. Schroth, W.; Billig, F.; Reinhold: G. Z. Chem. 1965, 5, 352-353.
25. Block, E.; Guo, C.; Thiruvazhi, M.; Toscano, P. J. J. Am. Chem. Soc. 1994, 116, 9403-9404.
26. (a) Koreeda, M.; Yang, W. J. Am. Chem. Soc. 1994, 116, 10793-10794.
27. (b) Koreeda, M.; Yang, W. Synlett 1994, 201-203.
28. (a) Block, E.; Birringer, M.; He, C. Angew. Chem., Int. Ed. Engl. 1999, 38, 1604-1607.
29. (b) A photograph of the trap appears in ref 8a.
30. (a) Gillies, J. Z.; Gillies, C. W.; Cotter, E. A.; Block, E.; DeOrazio, R. J. Mol. Spectrosc. 1996, 180, 139-144.
31. (b) For X-ray crystallographic studies of 1,2-dithiins, see references therein.
32. X-ray structure of dibenzo[c,e]-1,2-diselenin: Bryce, M. R.; Chesney, A.; Lay, A. K.; Batsanov, A. S.; Howard, J. A. K. J. Chem. Soc., Perkin Trans. 1 1996, 2451-2459.
33. (a) Block, E.; DeOrazio, R.; Guo, C.; Page, J.; Sheridan, R. S.; Toscano, J.; Towers, G. H. N.; Wang, C.-W.; Zhang, X. J. Am. Chem. Soc. 1996, 118, 4719-4720.
34. (b) Page, J. E.; Block, E.; Towers, G. H. N. Photochem. Photobiol. 1999, 70, 159-165.
35. (a) Preliminary reports: refs 6, 8a, 11b.
36. (b) Glass, R. S.; Pollard, J. R.; Schroeder, T. B.; Lichtenberger, D. L.; Block, E.; DeOrazio, R.; Guo, C.; Thiruvazhi, M. Phosphorus, Sulfur, Silicon Relat. Elements 1997, 120/ 121, 439-440.
37. (c) DeOrazio, R. M.S. Thesis, SUNY-Albany, 1996.
38. (d) Thiruvazhi, M. Ph.D. thesis, SUNY-Albany, 1993.
39. (e) Guo, C. M.S. thesis, SUNY-Alhany, 1994.
40. (f) Zhang, X. Ph.D. Thesis, SUNY-Albany, 1997.
41. Glass, R. S.; Gruhn, N. E.; Lichtenbcrger, D. L.; Lorance, E.; Pollard, J. R.; Birringer, M.; Block, E.; DeOrazio, R.; He, C.; Shan, Z.; Zhang, Z. J. Am. Chem. Soc. 2000, 122, 5065-5074.
42. (a) Schroth, W.; Dunger, S.; Billig, F.; Spitzner, R.; Herzschuh, R.; Vogt, A.; Jende, T.; Israel, G.; Barche, J.; Ströhl, D.; Sieler, J. Tetrahedron 1996, 52, 12677-12698.
43. (b) Bierer, D. E.; Dener, J. M.; Dubenko, L. G.; Gerber, R. E.; Litvak, J.; Peterli, S.; Peterli-Roth, P.; Truong, T. V.; Mao, G.; Bauer, B. E. J. Med. Chem. 1995, 38, 2628-2648.
44. Koreeda, M.; Wang, Y. J. Org. Chem. 1997, 62, 446-447.
45. Yang, W. Ph.D. Thesis, The University of Michigan, 1994.
46. Yamaguchi, S.; Jin, R.-Z.; Tamao, K.; Sato, F. J. Org. Chem. 1998, 63, 10060-2.
47. 8a (a) Burns, C. J.; Field, L. D.; Morgan, J.; Ridley, D. D.; Vignevich, V. Tetrahedron Lett. 1999, 40, 6489-6492. (b) Jia, X.; Zhang, Y.; Zhou, X. Tetrahedron Lett. 1994, 35, 8833-8834.
48. 8a (a) Burns, C. J.; Field, L. D.; Morgan, J.; Ridley, D. D.; Vignevich, V. Tetrahedron Lett. 1999, 40, 6489-6492. (b) Jia, X.; Zhang, Y.; Zhou, X. Tetrahedron Lett. 1994, 35, 8833-8834.
49. (a) Wynberg, H.; Wiersum, U. E. J. Org. Chem. 1965, 30, 1058-1060.
50. (b) Barton, T. J.; Hussman, G. P. J. Org. Chem. 1985, 50, 5881-5882.
51. Yin, J.; Jones, W. M. Tetrahedron 1995, 57, 4395-4406.
52. Hideura, D.; Urabe, H.; Sato, F. J. Chem. Soc., Chem. Commun. 1998, 271-272.
53. (a) Meinke, P. T.; Krafft, G. A.; Guram, A. J. Org. Chem. 1988, 53, 3632-3634.
54. (b) Barton, D. H. R.; Bridon, D.; Herve, Y.; Potier, P.; Thierry, J.; Zard, S. Z. A. Tetrahedron 1986, 42, 4983-4990.
55. Kates, M. J.; Schauble, J. H. J. Org. Chem. 1994, 59, 494-496.
56. Miki, Y.; Sugimoto, Y.; Yamadaya, S. Nippon Kagaku Kaishi 1993, 79.
57. Schroth, W.; Hintzsche, E.; Spitzner, R.; Ströhl, D.; Sieler, J. Tetrahedron 1995, 51, 13247-13260.
58. Wang, Y.; Koreeda, M. Synlett 1996, 885-886.
59. A stable 1,2-dithiin 1,1-dioxide has been prepared by a Diels-Alder route: Bard, M.; Meslin, J. C.; Quiniou, H. J. Chem. Soc., Chem. Commun. 1973, 672.
60. In contrast, unsaturated six-membered ring sultones undergo electrocyclic ring opening on photolysis: King, J. F.; Mayo, P. D.; Morkved, E.; Sattar, A. B. M.; Stoessl, A. Can. J. Chem. 1963, 41, 100-107.
61. A limited number of selenoseleninates are known: (a) Reich, H. J.; Hoeger, C. A.; Willis, W. W., Jr. J. Am. Chem. Soc. 1982, 104, 2936-2937. (b) Reich, H. J.; Hoeger, C. A.; Willis, W. W., Jr. Tetrahedron 1985, 41, 4771-4779. (c) Ishii, A.; Matsubayashi, S.; Takahashi, T.; Nakayama, J. J. Org. Chem. 1999, 64, 1084-1085.
62. A limited number of selenoseleninates are known: (a) Reich, H. J.; Hoeger, C. A.; Willis, W. W., Jr. J. Am. Chem. Soc. 1982, 104, 2936- 2937. (b) Reich, H. J.; Hoeger, C. A.; Willis, W. W., Jr. Tetrahedron 1985, 41, 4771-4779. (c) Ishii, A.; Matsubayashi, S.; Takahashi, T.; Nakayama, J. J. Org. Chem. 1999, 64, 1084-1085.
63. A limited number of selenoseleninates are known: (a) Reich, H. J.; Hoeger, C. A.; Willis, W. W., Jr. J. Am. Chem. Soc. 1982, 104, 2936- 2937. (b) Reich, H. J.; Hoeger, C. A.; Willis, W. W., Jr. Tetrahedron 1985, 41, 4771-4779. (c) Ishii, A.; Matsubayashi, S.; Takahashi, T.; Nakayama, J. J. Org. Chem. 1999, 64, 1084-1085.
64. (a) While the long wavelength maxima of 1c compared to saturated cyclic disulfides is unusual, it is noteworthy that a bicyclic dithiirane also has an absorption at 452 nm (∈ 104): Ishii, A.; Akasawa, T.; Maruta, T.; Nakayama, J.; Hoshino, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 777-779.
65. (b) Umezawa, T.; Sugihara, Y.; Ishii, A.; Nakayama, J. J. Am. Chem. Soc. 1998, 120, 12351-12352.
66. (c) Nakayama, J.; Yu, T.; Sugihara, Y.; Ishii, A. Chem. Lett. 1997, 499-500.
67. (d) Nakayama, J.; Nagasawa, H.; Sugihara, Y.; Ishii, A. J. Am. Chem. Soc. 1997, 119, 9077-9078.
68. (e) Nagasawa, H.; Sugihara, Y.; Ishii, A.; Nakayama, J. Bull. Chem. Soc. Jpn. 1999, 72, 1919-1926.
69. 25b
70. Luthra, N. P.; Odom, J. in The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1986; Vol. 1, pp 189-241.
71. (a) Cheeseman, J. R.; Trucks G. W.; Keith, T. A.; Frisch J. J. Chem. Phys. 1996, 104, 5497-5509 and references therein.
72. (b) Chesnut, D. B. Rev. Comput. Chem. 1996, 8, 245-297.
73. (c) Wiberg, K. B., J. Comput. Chem. 1999, 12, 1299-1303.
74. (d) Schreckenbach, G.; Ruiz-Morales, Y.; Ziegler, T. J. Chem. Phys. 1996, 104, 8605-8612.
75. (e) Buhl, M.; Thiel, W.; Fleischer, U.; Kutzelnigg, W. J. Phys. Chem. 1995, 99, 4000-4007.
76. 78Se isotopomers of 5c have been recently assigned with a pulsed-beam Fourier transform microwave spectrometer: Gillies, C. W., Nathan, C., Gillies, J. Z., Block, E., Birringer, M. Shan, Z., unpublished studies.
77. (a) Personal communication, W. Schroth.
78. (b) See Note Added in Proof in the accompanying paper (ref 12) for details on the X-ray structure of 1g.
79. 1,2-Diselenane UV spectra: Djerassi, C.; Wolf, H.; Bunnenberg, E. J. Am. Chem. Soc. 1962, 84, 4552-4561.
80. Jones, E.; Moodie, I. M. In Organic Syntheses; Wiley & Sons: New York, 1988; Collect. Vol. VI, pp 979-980.
81. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrewski, V. G.; Ortiz, S. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
82. Rathore, R.; Lindeman, S. V.; Kumar, A. S.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 6931-6939.
83. (a) Hammerich, O.; Parker, V. D. Acta Chem. Scand., Ser. B 1981, 35, 395-402.
84. (b) Olsen, B. A.; Evans, D. H. J. Am. Chem. Soc. 1981, 103, 839-843.
85. (c) Olsen, B. A.; Evans, D. H.; Agranat, I. J. Electroanal. Chem. 1982, 136, 139-148.
86. (d) Matsue, T.; Evans, D. H.; Agranat, I. J. Electroanal. Chem. 1984, 163, 137-143.
87. (e) Matsue, T.; Evans, D. H. J. Electroanal. Chem. 1984, 168, 287-298.
88. (a) Nelsen, S. F.; Echegoyen, L.; Evans, D. H. J. Am. Chem. Soc. 1975, 97, 3530-3532.
89. (b) Nelsen, S. F.; Echegoyen, L.; Clennan, E. L.; Evans, D. H.; Corrigan, D. A. J. Am. Chem. Soc. 1977, 99, 1130-1134.
90. Nelsen, S. F.; Clennan, E. L.; Evans, D. H. J. Am. Chem. Soc. 1978, 100, 4012-4019.
91. Nelsen, S. F. Acc. Chem. Res. 1981, 14, 131-138.
92. Dietrich, M.; Heinze, J.; Krieger, C.; Neugebauer, F. A. J. Am. Chem. Soc. 1996, 118, 5020-5030.
93. (a) Allendoerfer, R. D.; Rieger, P. H. J. Am. Chem. Soc. 1965, 87, 2336-2344.
94. (b) Huebert, B. J.; Smith, D. E. J. Electroanal. Chem. 1971, 31, 333-348.
95. Smith, W. H.; Bard, A. J. J. Electroanal. Chem. 1977, 76, 19-26.
96. Zweig, A.; Hoffman, A. K. J. Org. Chem. 1965, 30, 3997-4001.
97. Aso, Y.; Yui, K.; Miyoshi, T.; Otsubo, T.; Ogura, F.; Tanaka, J. Bull. Chem. Soc. Jpn. 1988, 61, 2013-2018.
98. Bock, H.; Brahler, G.; Dauplaise, D.; Meinwald, J. Chem. Ber. 1981, 114, 2622-2631.
99. Sandman, D. J.; Ceasar, G. P.; Nielsen, P.; Epstein, A. J.; Holmes, T. J. J. Am. Chem. Soc. 1978, 100, 202-206.
100. Lichtenberger, D. L.; Johnston, R. L.; H nkelmann, K.; Suzuki, T.; Wudl, F. J. Am. Chem. Soc. 1990, 112, 3302-3307.
101. Glass, R. S. Top. Curr. Chem. 1999, 265, 1-87.
102. Latypova, V. Z.; Chichirov, A. A.; Jouikov, V. V.; Yakovleva, O. G.; Vinckurova, R. J.; Ustyugova, I. A.; Kargin, Yu, M. Zh. Obshch. Khim. 1989, 59, 1344-1348.
103. (a) Slender, K.-W.; Klar, G.; Knittel, E. Z. Naturforsch. B 1985, 40, 774-781.
104. (b) Canou, M.; Douadi, T.; Simonet, J. New J. Chem. 1996, 20, 1031-1039.
105. (a) Dakova, B.; Carbonnelle, P.; Lamberts, L.; Evers, M. Electrochim. Acta 1992, 37, 2077-2082.
106. (b) Dakova, B.; Carbonelle, P.; Walcarius, A.; Lamberts, L.; Evers, M. Electrochim. Acta 1992, 37, 725-729.
107. Muller, R.; Lamberts, L.; Evers, M. J. Electroanal. Chem. 1996, 401, 183-189.
108. (a) Bock, H.; Kaim, W. Acc. Chem. Res. 1982, 15, 9-17.
109. (b) Giordan, J.; Bock, H. Chem. Ber. 1982, 115, 2548-2559.
110. Bock, M.; Hierholzer, B.; Rittmeyer, P. Z. Naturforsch. B 1989, 44, 187-204.
111. (a) Gillespie, R. J.; Ireland, P. R.; Vekris, J. E. Can. J. Chem. 1975, 53, 3147-3152.
112. (b) Roesky, H. W.; Hamza, A. Angew. Chem., Int. Ed. Engl. 1976, 15, 226.
113. (c) Gillespie, R. J.; Kent, J. P.; Sawyer, J. F. Inorg. Chem. 1981, 20, 3784-3799.
114. (d) Cameron, T. S.; Haddon, R. C.; Mattar, S. M.; Parsons, S.; Passmore, J.; Ramirez, A. P. J. Chem Soc., Chem. Commun. 1991, 358-360.
115. (e) Cameron, T. S.; Haddon, R. C.; Mattar, S. M.; Parsons, S.; Passmore, J.; Ramirez, A. P. J. Chem. Soc., Dalton Trans. 1992, 1563-1572.
116. (f) Cameron, T. S.; Haddon, R. C.; Mattar, S. M.; Parsons, S.; Passmore, J.; Ramirez, A. P. Inorg. Chem. 1992, 31, 2274-2279.
117. (g) Wolmershäuser, G.; Heckmann, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 779-780.
118. (h) Ogawa, S.; Kikuchi, T.; Niizuma, S.; Sato, R. J. Chem. Soc., Chem. Commun. 1994, 1593-1594.
119. (i) Ogawa, S.; Kikuchi, T.; Sasaki, A.; Chida, S.; Sato, R. Tetrahedron Lett. 1994, 35, 5469-5472.
120. (j) Nishinaga, T.; Wakamiya, A.; Komatsu, K. Tetrahedron Lett. 1999, 40, 4375-4378.
121. (a) Buddensiek, D.; Köpke, B.; Vöss, J. Chem. Ber. 1987, 120, 575-581.
122. (b) Russell, G. A.; Law, W. C. In Sulfur-Centered Reactive Intermediates in Chemistry and Biology, Chatgilialoglu, C., Asmus, K.-D., Eds.; Plenum: New York, 1991; pp 117-183.
123. Zhu-Ohlbach, Q.; Gleiter, R.; Rominger, F.; Schmidt, H.-L.; Reda, T. Eur. J. Org. Chem. 1998, 2409-2416.