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Volumn 133, Issue 15, 2011, Pages 5843-5852

Sulfur monoxide transfer from peri -substituted trisulfide-2-oxides to dienes: Substituent effects, mechanistic studies and application in thiophene synthesis

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC SULFOXIDE; DITHIOLS; FORMAL SYNTHESIS; IN-SITU TRAPPING; KINETIC STUDY; MECHANISTIC STUDIES; NAPHTHALENE RING; NATURALLY OCCURRING; O-METHOXY; RING STRAINS; ROOM TEMPERATURE; SUBSTITUENT EFFECT; THIONYL CHLORIDES;

EID: 79954525913     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja108865w     Document Type: Article
Times cited : (47)

References (123)
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    • The more common "trisulfide" and "disulfide" nomenclature has been used throughout, rather than the IUPAC recommended disulfane, trisulfane, etc. For a discussion and review of the chemistry of organic polysulfanes, see Steudel, R. Chem. Rev. 2002, 102, 3905-3945
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    • An earlier report on formation of dithietes from trithiole-2-oxides also considered formal release of SO in a mechanistic hypothesis
    • An earlier report on formation of dithietes from trithiole-2-oxides also considered formal release of SO in a mechanistic hypothesis: Simmons, H. E.; Blomstrom, D. C.; Vest, R. D. J. Am. Chem. Soc. 1962, 84, 4772-4781
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    • Increasing the equivalence of tert -butylbromide results in overalkylation to 2,4,7-tri- tert -butylnaphtho[1,8- cd ][1,2]dithiole (44). See Supporting Information for details
    • Increasing the equivalence of tert -butylbromide results in overalkylation to 2,4,7-tri- tert -butylnaphtho[1,8- cd ][1,2]dithiole (44). See Supporting Information for details.
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    • 3 at rt gave a mixture of 21 (10%) and 1,6-dibromo-2,7- dimethoxynaphthalene (45) (35%). The structure of the latter compound was proven by X-ray crystallography. (46) See Supporting Information for details.
    • 3 at rt gave a mixture of 21 (10%) and 1,6-dibromo-2,7- dimethoxynaphthalene (45) (35%). The structure of the latter compound was proven by X-ray crystallography. (46) See Supporting Information for details.
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    • Chlorination of the electron-rich naphthalene ring system may be a problem under these conditions.
    • Chlorination of the electron-rich naphthalene ring system may be a problem under these conditions.
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    • CCDC 171805 (15), CCDC 794194 (16), CCDC 794195 (17), CCDC 794196 (28), CCDC 794197 (29), and CCDC 794198 (45) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC 171805 (15), CCDC 794194 (16), CCDC 794195 (17), CCDC 794196 (28), CCDC 794197 (29), and CCDC 794198 (45) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ datarequest/cif.
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    • We have shown by cyclic voltammetry that disulfide 20 is easier to oxidize than 18, as reflected in the first oxidation potential: see Supporting Information for details. Naphtho[1,8- cd ][1,2]dithiole (18) is known to form charge-transfer donor-acceptor complexes with TCNE (25a) and TCNQ
    • We have shown by cyclic voltammetry that disulfide 20 is easier to oxidize than 18, as reflected in the first oxidation potential: see Supporting Information for details. Naphtho[1,8- cd ][1,2]dithiole (18) is known to form charge-transfer donor-acceptor complexes with TCNE (25a) and TCNQ: Sandman, D. J.; Ceasar, G. P.; Nielsen, P.; Epstein, A. J.; Holmes, T. J. J. Am. Chem. Soc. 1978, 100, 202-206
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    • For alternative conditions for the nitration of disulfide 18 to prepare a mixture of nitroarenes 28 and 29 and their independent characterization, including single crystal X-ray analyses, (46) see Supporting Information.
    • For alternative conditions for the nitration of disulfide 18 to prepare a mixture of nitroarenes 28 and 29 and their independent characterization, including single crystal X-ray analyses, (46) see Supporting Information.
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    • 2 accounts for the mass loss while elemental sulfur remains.
    • 2 accounts for the mass loss while elemental sulfur remains.
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    • For related dehydrations of 1,3-dihydrobenzo[ c ]thiophene 2-oxides to 1,3-benzo[ c ]thiophenes see
    • For related dehydrations of 1,3-dihydrobenzo[ c ]thiophene 2-oxides to 1,3-benzo[ c ]thiophenes see: Cava, M. P.; Pollack, N. M. J. Am. Chem. Soc. 1966, 88, 4112-4113
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    • 2, the dimer of SO, has also been proposed as a dienophile towards a reactive diene. (21)
    • 2, the dimer of SO, has also been proposed as a dienophile towards a reactive diene. (21)
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    • For a synthesis of 40 based on copper-catalyzed rearrangement of a vinyl episulfide to a 2,5-dihydrothiophene, followed by oxidation to the thiophene and N -deprotection see
    • For a synthesis of 40 based on copper-catalyzed rearrangement of a vinyl episulfide to a 2,5-dihydrothiophene, followed by oxidation to the thiophene and N -deprotection see: Rogers, E.; Araki, H.; Batory, L. A.; McInnis, C. E.; Njardarson, J. T. J. Am. Chem. Soc. 2007, 129, 2768-2769
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    • Rogers, E.1    Araki, H.2    Batory, L.A.3    McInnis, C.E.4    Njardarson, J.T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.