1,2-Dithiines and precursors, XVI: Synthesis, structure, and reactivity of non-anellated 1,2-dithiines

Tetrahedron

Volumn 52, Issue 39, 1996, Pages 12677-12698

  Schroth, Werner ^b   Dunger, Simona ^b   Billig, Frank ^b   Spitzner, Roland ^b   Herzschuh, Rainer ^b   Vogt, Almut ^b   Jende, Thomas ^b   Israel, Gunter ^b   Barche, Jens ^b   Ströhl, Dieter ^b   Sieler, Joachim ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DITHIIN DERIVATIVE; ORGANOSULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTROPHOTOMETRY; STEREOCHEMISTRY;

EID: 0001150654     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00752-1     Document Type: Article

References (107)

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44. 8. Cf. exceptions according to Scheme 6 and in: a) Behringer, H.; Meinetsberger, E. Liebigs Ann. Chem. 1981, 1729-1750; ibid. 1981, 1928-1959; ibid. 1982, 315-341.
45. 8. Cf. exceptions according to Scheme 6 and in: a) Behringer, H.; Meinetsberger, E. Liebigs Ann. Chem. 1981, 1729-1750; ibid. 1981, 1928-1959; ibid. 1982, 315-341.
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50. 1g).
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52. - Dshemilew, U. M.; Baibulatowa, N. S.; Tkatschenko, T. K.; Kumakowa, R. W. ibid. 1987, 1918. - Distillable non-coloured oil without any extrusion of sulfur, obtained by a cobalt catalyzed reaction of 1-pentyne with carbon disulfide or propyne with sulfur/butyl chloride under vigorous conditions (150°C, 6 h). In accord with the indication of that two isomers 2,4-and 2,5-dibutyl-1,4-dithiines should be present.
53. 11. Cf. Review: a) Shostakovskii, M. F.; Bogdanova, A. V. The Stereochemistry of Diacetylenes, John Wiley & Sons, New York, Toronto, 1974, especially 109-118.
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58. 4 in THF seems to be a convenient method in the aromatic substituted series: Freeman, F.; Lu, H.; Rodriguez, E. Sulfur Lett. 1995, 18, 243-257.
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60. z-overlapping between the sulfur atom with the adjacent carbon atom.
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62. - Cf. attempts by direct sulfurization of 1,4-diketones: b) Freeman, F.; Kim, D. S. H. L.; Rodriguez, E. J. Org. Chem. 1992, 57, 1722-1727.
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65. max = 509 nm (1g ε = 3.75) of 3,6-bis(diphenylmethylen)-amino-4,5-dicyano-1,2-dithiine: a) Moran, J. R.; Huisgen R.; Kalwinsch, I. Tetrahedron Lett. 1985, 26, 1849-1852.
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71. collectd.: 3440; final R indices [I > 2σ > (I)]: R1 = 0.0369, wR2 = 0.0900; R indices (all data): R1 = 0.0736, wR2 = 0.1039; diffractometer: STOE. - Tables of the atomic coordinates, thermal parameters, bond lengths, and angles have been deposited at the Cambridge Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW. The X-ray data are available on request from the Director of the CCDC by quoting the literature citation of this paper.
72. W = 0.054; diffractometer: HUBER; program: SHELX76, SHELXS86: - Further details of the crystal structure analysis may be obtained from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (FRG), on quoting the depository number CSD-400847 and the names of the authors (J. Sieler).
73. 1h,i,k.
74. 18a).
75. - After completion of this paper, we learned that also microwave spectroscopy reveals a nonplanar structure of the parent compound 6a with a torsion angle of 53.9°: c) Block, E; Page, J.; Toscano, J., P; Wang, C.-X.; Zhang, X.; DeOrazio, R.; Guo, C.; Sheridan, R. S.; Towers, G. H. N. J. Am. Chem. Soc. 1996, 118, 4719-4720.
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85. -3/solvent. The quantum yields are constant up to conversions of 70%.
86. 11 (there note 14); error limits generally ±0.1.
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88. 24c.
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95. 34. A further possible relationship, the suggested course of the reaction of ethoxycarbonyl azide with thiophenes to N-ethoxycarbonylpyrroles, expelling sulfur, should be considered: Hafner, K.; Kaiser, W. Tetrahedron Lett. 1964, 2185-2190. - Lindley, J. M.; Meth-Cohn, O.; Suschitzky, H. J. Chem. Soc. Perkin Trans. I 1978, 1198-1204. - Colburn, V. M.; Iddon, B.; Suschitzky, H.; Gallagher, P. T. ibid. 1979, 1337-1340.
96. 34. A further possible relationship, the suggested course of the reaction of ethoxycarbonyl azide with thiophenes to N-ethoxycarbonylpyrroles, expelling sulfur, should be considered: Hafner, K.; Kaiser, W. Tetrahedron Lett. 1964, 2185-2190. - Lindley, J. M.; Meth-Cohn, O.; Suschitzky, H. J. Chem. Soc. Perkin Trans. I 1978, 1198-1204. - Colburn, V. M.; Iddon, B.; Suschitzky, H.; Gallagher, P. T. ibid. 1979, 1337-1340.
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103. 39. Rapid heating, otherwise formation of the corresponding thiophene 12.
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