1,2-Dithiins and precursors, XVII: Synthesis and properties of thieno anellated 1,2-dithiins, structural influence on colour

Tetrahedron

Volumn 53, Issue 22, 1997, Pages 7509-7528

  Schroth, Werner ^a   Hintzsche, Ekkehard ^a   Jordan, Hartwig ^a   Jende, Thomas ^a   Spitzner, Roland ^a   Thondorf, Iris ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSULFUR DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; LIGHT ABSORPTION; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTROPHOTOMETRY; STRUCTURE ACTIVITY RELATION;

EID: 0030926912     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00439-0     Document Type: Article

References (70)

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2. Obviously based on n→σ* or σ→σ* transition, cf. quantumtheoretical calculations a) Cimiraglia, R.; Fabian, J.; Hess jr., B. A. J. Mol. Struct. (Theochem) 1991, 230, 287-293.
3. b) Mann, M.; Fabian, J. ibid. 1995, 331, 51-61. - Cf. also the discussion of no bond resonance with the ring-opened dithioxo valence isomer 1′ as reason (a parallelism with bathochromic shifts of the C=S group by conjugation should be suggested):
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6. d) Moran, J. R.; Huisgen, R.; Kalwinsch, I. Tetrahedron Lett. 1985, 26, 1849-1852; cf. also: Huisgen, R.; Kalwinsch, I.; Morán, J.; Nöth, H.; Rapp, J. Liebigs Ann/Recueil 1997, submitted (W.S. is indebted to Professor Huisgen for communication of the results prior to publication). (equation presented)
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10. max = 486 nm:
11. max = 447 nm) of about 40 nm related to 2 (R = H):
12. c) Schroth, W.; Jordan, H.; Spitzner, R. Tetrahedron Lett. 1995, 36, 1421-1424.
13. max (1g ε) = 276 (3.79), 305 (3.46, sh) nm.
14. max (1g ε) = 276 (3.79), 305 (3.46, sh) nm.
15. a) Schroth, W.; Spitzner, R.: hitherto unpublished work
16. b) In this connection we point out that dipyrazolo-1,2-dithiin 59, the first claimed 1,2-dithiin representative (Michaelis, A. Liebigs Ann. Chem. 1908, 361, 251-301), was shown to be the 1,4-isomer 60. (equation presented)
17. Concerning the questionable aromatic behaviour of thiophene cf. the critical review: Iddon, B. Heterocycles 1983, 20, 1127-1171.
18. 3,6-Diphenylthieno[3,2-c][1,2]dithiin (5b): a) Behringer, H.; Meinetsberger, E. Liebigs Ann. Chem. 1981, 1928-1959. - 3,4,6,7-Tetraphenylthieno[3,2-c][1,2]dithiin (5c):
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21. 8b (especially p. 1732)]: (equation presented)
22. b) Cf. also the formation of 3,4:6,7-bis(ethylenedithio)thieno[3,2-c][1,2]dithiin (62) by a comparable reaction of the correspondingly substituted 1,2-dithiolium salt 61 with Zn: Tanaka, M.; Ishida, T.; Nogami, T.; Yoshikawa, H.; Yasui, M.; Iwasaki, F. Bull. Chem. Soc. Jpn. 1995, 68, 1193-1199. It is noteworthy that this thieno anellated 1,2-dithiin shows its long wave absorption maximun at 472 nm. (equation presented)
23. Avoiding lithiation at 2-position and consecutive reactions (e.g. ring opening), cf. a) Brandsma, L.; Verkruijsse, H. D. Preparative Polar Organometallic Chemistry, Vol. 1, Springer Verlag, Berlin - Heidelberg 1987.
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29. Cf. pathway by thiolation with Sg: Prim, D.; Kirsch, G. J. Chem. Soc., Perkin Trans. I 1994, 2603-2606.
30. Comparable strategy based on transformation of chlorovinylaldehydes to methylthiovinylaldehydes, subsequently to methylthiovinylacetylenes and finally to thiophenes: Frejd, T.; Karlsson, J. O.; Gronowitz, S. J. Org. Chem. 1981, 46, 3132-3135.
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34. +]}.
35. b) G. Israel, University Halle, unpublished results. (equation presented)
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37. Cf. preliminary note: Schroth, W.; Hintzsche, E.; Felicetti, M.; Spitzner, R.; Sieler, J.; Kempe, R. Angew. Chem. 1994, 106, 808-810; Angew. Chem. Int. Ed. Engl. 1994, 33, 739-741.
38. Cf. preliminary note: Schroth, W.; Hintzsche, E.; Felicetti, M.; Spitzner, R.; Sieler, J.; Kempe, R. Angew. Chem. 1994, 106, 808-810; Angew. Chem. Int. Ed. Engl. 1994, 33, 739-741.
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41. -1; program: SHELX.
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43. c) Further details of the structure determination (e.g. structure factors) have been deposited within the relevant database and can be accessed as Collection No. 400129 or ordered from the Fachinformationszentrum Karlsuhe, D-76344 Eggenstein-Leopoldshafen.
44. 19).
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48. 2S]}.
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50. 19,25.
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53. -1 was reached. For computation of rotational barriers of the free thiols 54 and 55 the torsion angle around the interconnecting C,C-bond was varied in steps of 5° covering the range of 0° to 360°. In the case of 32b and the (hypothetical) 52 the grid search was performed by modifying this torsion angle between 15° and 45° in steps of 1°.
54. -1; program: SHELX.
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66. 3 in accord with the steric assignment; cf. Magriotis, P. A.; Brown, J. T.; Scott, M. E. Tetrahedron Lett. 1991, 32, 5047-5050.
67. a) Chapman, N. B.; Hughes, C. G., Scrowston, R. M. J. Chem. Soc. C 1970, 2431-2435.
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