Unprecedented conversion of triethylamine and disulfur dichloride into a thienopentathiepin and a heptathiocane

Organic Letters

Volumn 5, Issue 11, 2003, Pages 1939-1942

  Konstantinova, Lidia S ^a   Rakitin, Oleg A ^a   Rees, Charles W ^b   Souvorova, Ljudmila I ^a   Golovanov, Denis G ^c   Lyssenko, Konstantin A ^c  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; CHEMICAL COMPOUND; CHLOROFORM; DISULFUR DICHLORIDE; HEPTATHIOCANE; SULFUR DERIVATIVE; THIENOPENTATHIEPINE; THIEPIN DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION;

EID: 0141741395     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034513x     Document Type: Article

References (11)

1. Konstantinova, L. S.; Rakitin, O. A.; Rees C. W. Mendeleev Commun. 2001, 11, 165.
2. Barriga, S.; Konstantinova, L. S.; Marcos, C. F.; Rakitin, O. A.; Rees, C. W.; Torroba, T.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1999, 2237.
3. Rees, C. W.; White, A. J. P.; Williams, D. J.; Rakitin, O. A.; Marcos, C. F.; Polo, C.; Torroba, T. J. Org. Chem. 1998, 63, 2189. Rees, C. W.; White, A. J. P.; Williams, D. J.; Rakitin, O. A.; Konstantinova, L. S.; Marcos, C. F.; Torroba, T. J. Org. Chem. 1999, 64, 5010; Konstantinova, L. S.; Obruchnikova, N. V.; Rakitin, O. A.; Rees C. W.; Torroba T. J. Chem. Soc., Perkin Trans. 1, 2000, 3421.
4. Rees, C. W.; White, A. J. P.; Williams, D. J.; Rakitin, O. A.; Marcos, C. F.; Polo, C.; Torroba, T. J. Org. Chem. 1998, 63, 2189. Rees, C. W.; White, A. J. P.; Williams, D. J.; Rakitin, O. A.; Konstantinova, L. S.; Marcos, C. F.; Torroba, T. J. Org. Chem. 1999, 64, 5010; Konstantinova, L. S.; Obruchnikova, N. V.; Rakitin, O. A.; Rees C. W.; Torroba T. J. Chem. Soc., Perkin Trans. 1, 2000, 3421.
5. Rees, C. W.; White, A. J. P.; Williams, D. J.; Rakitin, O. A.; Marcos, C. F.; Polo, C.; Torroba, T. J. Org. Chem. 1998, 63, 2189. Rees, C. W.; White, A. J. P.; Williams, D. J.; Rakitin, O. A.; Konstantinova, L. S.; Marcos, C. F.; Torroba, T. J. Org. Chem. 1999, 64, 5010; Konstantinova, L. S.; Obruchnikova, N. V.; Rakitin, O. A.; Rees C. W.; Torroba T. J. Chem. Soc., Perkin Trans. 1, 2000, 3421.
6. Konstantinova, L. S.; Rakitin, O. A.; Rees C. W. Mendeleev Commun. 2001, 11, 167.
7. Tokitoh, N.; Ishizuka, H.; Ando, W. Chem. Lett. 1988, 657.
8. Chenard, B. L.; Harlow, R. L.; Johnson, A. L.; Vladuchick, S. A. J. Am. Chem. Soc. 1985, 107, 3871.
9. 2 mixtures). Thienopentathiepins 2 and heptathiocanes 3 were isolated with the yields indicated: 2a (30%), 2b (2%), 2c (1%), 2d (28%), 2e (21%), 2f (8%), 3a (4%), 3b (3%), 3c (10%), and 3d (3%).
10. Konstantinova, L. S.; Rakitin, O. A.; Rees C. W. Chem. Commun. 2002, 1204.
11. Greer A. J. Am. Chem. Soc. 2001, 113, 10379 and references therein.