Pummerer reaction of 4,7-di-tert-butyl-3H,8H-1,2,5,6-dithiadiazocine 1-oxide; formation of 1,4-dithiins

Journal of Sulfur Chemistry

Volumn 25, Issue 1, 2004, Pages 13-19

  Nakayama, Juzo ^a   Iida, Shuhei ^a   Sugihara, Yoshiaki ^a   Ishii, Akihiko ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

1,4 Dithiins; DFT calculations; Eight membered heterocycles; Pummerer reaction; Thiosulfinates

Indexed keywords

1,4-DITHIINS; DFT CALCULATION; EIGHT-MEMBERED HETEROCYCLE; HETEROCYCLES; PUMMERER REACTION; THIOSULFINATES;

1,4 DITHIANE DERIVATIVE; 1,4 DITHIIN DERIVATIVE; 4,7 DI TERT BUTYL 3H,8H 1,2,5,6 DITHIADIAZOCINE 1 OXIDE; PYRIDAZINE DERIVATIVE; SULFONIC ACID DERIVATIVE; THIADIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DEHYDRATION; DRUG MIXTURE; PRODUCT RECOVERY; PROTON NUCLEAR MAGNETIC RESONANCE; PUMMERER REACTION; REACTION ANALYSIS; REACTION OPTIMIZATION; STRUCTURE ANALYSIS;

EID: 1842481405     PISSN: 17415993     EISSN: None     Source Type: Journal    
DOI: 10.1080/17415990410001658946     Document Type: Article

References (21)

1. Recent papers. (a) Ishii, A., Yamashita, R., Saito M. and Nakayama, J., J. Org. Chem., 68, 1555 (2003).
2. (b) Ono, Y., Sugihara, Y., Ishii, A. and Nakayama, J., Bull. Chem. Soc. Jpn, 76, 613 (2003).
3. (c) Nakayama, J., Furuya, T., Ishii, A., Sakamoto, A., Otani, T. and Sugihara, Y., Bull. Chem. Soc. Jpn, 76, 619 (2003).
4. (d) Otani, T., Takayama, J., Sugihara, Y., Ishii, A. and Nakayama, J., J. Am. Chem. Soc., 125, 8255 (2003).
5. (e) Takayama, J., Fukuda, S., Sugihara, Y., Ishii, A. and Nakayama, J., Tetrahedron Lett., 44, 5159 (2003).
6. (f) Tanaka, S., Sugihara, Y., Sakamoto, A., Ishii, A. and Nakayama, J., J. Am. Chem. Soc., 125, 9024 (2003).
7. (g) Ono, Y., Sugihara, Y., Ishii, A. and Nakayama, J., J. Am. Chem. Soc., 125, 12114 (2003).
8. (h) Takayama, J., Sugihara, Y., Ishii, A. and Nakayama, J., Tetrahedron Lett., 44, 7893 (2003).
9. Matsuda, T. and Takada, Y., Phosphous Sulfur, 1, 75 (1976).
10. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Zakrzewski, V. G., Montgomery, J. A., Jr., Stratmann, R. E., Burant, J. C., Dapprich, S., Millam, J. M., Daniels, A. D., Kudin, K. N., Strain, M. C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P. Y., Cui, Q., Morokuma, K., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Cioslowski, J., Ortiz, J. V., Baboul, A. G., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P. M. W., Johnson, B. G., Chen, W., Wong, M. W., Andres, J. L., Head-Gordon, M., Replogle, E. S. and Pople, J. A., Gaussian 98 (Revision A.7) (Gaussian, Inc., Pittsburgh, PA, 1998).
11. (a) Sataty, I., J. Heterocycl. Chem., 7, 431 (1970).
12. (b) Nakayama, J., Konishi, T., Ishii, A. and Hoshino, M., Bull. Chem. Soc. Jpn, 62, 2608 (1989).
13. (a) Asinger, F., Thiel, M., Peschel, G. and Meincke, K.-H., Liebigs Ann. Chem., 619, 145 (1858).
14. (b) Bock, H., Rittmeyer, R. and Stein, U., Chem. Ber., 119, 3766 (1986).
15. (c) Nakayama, J., Choi, K. S., Yamaoka, S. and Hoshino, M., Heterocycles, 29, 391 (1989).
16. Meijer, J., Vermeer, P., Verkruijsse, H. D. and Brandsma, L., Recl. Trav. Chim. Pays-Bas, 92, 1326 (1973).
17. (a) Nakayama, J., Masui, N., Sugihara, Y. and Ishii, A., Bull. Chem. Soc. Jpn, 71, 1181 (1998) (and references cited therein).
18. (b) Gasper, P. P., Harrison, J. F. and Herold, B. J., In: Kirmse, W. (Ed.), Carbene Chemistry (Academic Press, New York and London, 1971), 2nd ed., Chap. 9, pp. 375.
19. Kirmse, W., Eur. J. Org. Chem., 2193 (2002).
20. Barker, H. R. and Barkenbus, C., J. Am. Chem. Soc., 58, 262 (1936).
21. Nakayama, J., Motoyama, H., Machida, H., Shimomura, S. and Hoshino, M., Heterocycles, 22, 1527 (1984).