Selective Syntheses of Bis[1,2]dithiolo[1,4]thiazines and Bis[1,2]dithiolopyrroles from Hünig's Base

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2189-2196

  Rees, Charles W ^a   White, Andrew J P ^a   Williams, David J ^a   Rakitin, Oleg A ^b   Marcos, Carlos F ^c   Polo, Cecilia ^c   Torroba, Tomás ^c  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

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

^c UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001441401     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971864e     Document Type: Article

References (38)

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26. Some recent examples of THF ring opening reactions are: (a) Namy, J.-L.; Colomb, M.; Kagan, H. B. Tetrahedron Lett. 1994, 35, 1723. (b) Boisson, C.; Berthet, J. C.; Lance, M.; Nierlich, M.; Ephritikhine, M. J. Chem. Soc., Chem. Commun. 1996, 2129.
27. Some recent examples of THF ring opening reactions are: (a) Namy, J.-L.; Colomb, M.; Kagan, H. B. Tetrahedron Lett. 1994, 35, 1723. (b) Boisson, C.; Berthet, J. C.; Lance, M.; Nierlich, M.; Ephritikhine, M. J. Chem. Soc., Chem. Commun. 1996, 2129.
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29. In the absence of DABCO, yields are calculated on the basis of 15 mol of Hünig's base giving 1 mol of product and 14 mol of Hünig's base hydrochloride (cf. Scheme 3).
30. Huisgen, R.; Mack, W.; Anneser, E. Angew. Chem., 1961, 73, 656. Boberg, F.; Knoop, J. Liebigs Ann. Chem., 1967, 708, 148. Kim, J. N.; Ryu, E. K. Tetrahedron Lett. 1993, 34, 8283.
31. Huisgen, R.; Mack, W.; Anneser, E. Angew. Chem., 1961, 73, 656. Boberg, F.; Knoop, J. Liebigs Ann. Chem., 1967, 708, 148. Kim, J. N.; Ryu, E. K. Tetrahedron Lett. 1993, 34, 8283.
32. Huisgen, R.; Mack, W.; Anneser, E. Angew. Chem., 1961, 73, 656. Boberg, F.; Knoop, J. Liebigs Ann. Chem., 1967, 708, 148. Kim, J. N.; Ryu, E. K. Tetrahedron Lett. 1993, 34, 8283.
33. Pinnick, H. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 221.
34. McKinnon, D. M. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, Chapter 4.31. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Sci.: Oxford, 1996; Vol. 3, Chapter 3.11.
35. McKinnon, D. M. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, Chapter 4.31. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Sci.: Oxford, 1996; Vol. 3, Chapter 3.11.
36. Bohle, M.; Liebscher, J. Adv. Heterocycl. Chem. 1996, 65, 39.
37. SHELXTL PC version 5.03, Siemens Analytical X-Ray Instruments, Inc., Madison, WI, 1994.
38. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.