Polar cycloaddition of monocyclic 1,2-thiazinylium salt and transformation of the cycloadducts to 1,2-azathiabenzenes

Tetrahedron Letters

Volumn 40, Issue 8, 1999, Pages 1505-1508

  Shimizu, Hiroshi ^a   Hatano, Takashi ^a   Matsuda, Takayuki ^a   Iwamura, Tatsunori ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

1,2 azathiabenzene; 1,2 thiazinylium salt; Polar cycloaddition

Indexed keywords

1,2 AZATHIABENZENE; 1,2 THIAZINYLIUM; BENZENE DERIVATIVE; INORGANIC SALT; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

EID: 0033582789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02663-X     Document Type: Article

References (9)

1. (a) H. Shimizu, S. Miyazaki, T. Kataoka, M. Hori and O. Muraoka, J. Chem. Soc., Perkin Trans. 1, 1994, 3129.
2. (b) H. Shimizu, S. Miyazaki, T. Kataoka and M. Hori, J. Chem. Soc., Perkin Trans. 1, 1995, 1583.
3. (c) H. Shimizu, S. Miyazaki and T. Kataoka, J. Chem. Soc., Perkin Trans. 1, 1996, 2227.
4. (d) H. Shimizu, S. Miyazaki and T. Kataoka, Tetrahedron, 1997, 53, 4611.
5. H. Shimizu, T. Hatano, T. Matsuda and T. Iwamura, Tetrahedron Lett., 1999, 40, 95.
6. L. Wald and W. Wucherpfennig, Ann. Chem., 1971, 746, 28.
7. 3) δ: 32.7(t), 38.2(t), 84.5(s), 126.3(d), 126.4(d), 127.8(d), 127.9(d), 128.2(d), 128.3(d), 128.5(d), 128.7(d), 128.8(d), 129.3(d), 129.4(s), 132.4(s), 133.7(s), 134.7(s), 137.1(s), 142.0(s), 142.7(s), 161.1(s), 165.0(d).
8. The MO calculation of 4,5-diphenyl-1,2-thiazinylium cation was performed with the PM3 hamiltonian by "WinMOPAC v2.0 (Fujitsu Ltd.) for the Windows 95 (Microsoft Inc.)", which is based on the MOPAC97 of Dr. J.J.P. Stewart and Fujitsu Ltd., Tokyo, Japan.
9. 1b, 1c