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Volumn 36, Issue 8, 1997, Pages 878-881

Studies of the First S-Position Isomer of Bis(ethylenedithio)tetrathiafulvalene

Author keywords

Cations; Conducting materials; Heterocycles; Radical ions; Sulfur; Tetrathiafulvalenes

Indexed keywords


EID: 0030916485     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199708781     Document Type: Article
Times cited : (24)

References (49)
  • 2
    • 5444247176 scopus 로고
    • and references therein
    • b) J. Garin, Adv. Heterocycl. Chem. 1995, 62, 249-304, and references therein.
    • (1995) Adv. Heterocycl. Chem. , vol.62 , pp. 249-304
    • Garin, J.1
  • 6
    • 12044251254 scopus 로고
    • a) D. Jérome, Science 1991, 252, 1509-1514;
    • (1991) Science , vol.252 , pp. 1509-1514
    • Jérome, D.1
  • 11
    • 3142592441 scopus 로고
    • and references therein
    • Y. Misaki, N. Higuchi, H. Fujiwara, T. Yamabe, T. Mori, H. Mori, S. Tanaka, Angew. Chem. 1995, 107, 1340-1343; Angew. Chem. Int. Ed. Engl. 1995, 34, 1222-1225, and references therein.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1222-1225
  • 15
    • 0001740940 scopus 로고    scopus 로고
    • For conducting salts of sulfur-rich TTF derivatives, see also a) M. Sallé, M. Jubault, A. Gorgues, K. Boubekeur, M. Fourmigué, P. Batail, E. Canadell, Chem. Mater. 1993, 5, 1196-1198; b) M. Sallé, A. Gorgues, M. Jubault, K. Boubekeur, P. Batail, R. Carlier, Bull. Soc. Chim. Fr. 1996, 133, 417-426.
    • (1996) Bull. Soc. Chim. Fr. , vol.133 , pp. 417-426
    • Sallé, M.1    Gorgues, A.2    Jubault, M.3    Boubekeur, K.4    Batail, P.5    Carlier, R.6
  • 19
    • 0027554914 scopus 로고
    • The difficulties of generating a good leaving group from the hydroxymethyl functionality directly attached to the TTF framework have been previously pointed out. To our knowledge, only the reaction of trifluoroacetic anhydride with 2-(hydroxymethyl)-TTF to afford the trifluoracetate leaving group has been described: T. Nozdryn, D. Clémenceau, J. Cousseau, V. Morisson, A. Gorgues, J. Orduna, S. Uriel, J. Garin, Synth. Met. 1993, 55-57, 1768-1771.
    • (1993) Synth. Met. , vol.55-57 , pp. 1768-1771
    • Nozdryn, T.1    Clémenceau, D.2    Cousseau, J.3    Morisson, V.4    Gorgues, A.5    Orduna, J.6    Uriel, S.7    Garin, J.8
  • 20
    • 85077634689 scopus 로고
    • Reviews: a) O. Mitsunobu, Synthesis 1981, 1-28; b) D. L. Hughes, Org. Reac. 1992, 42, 335-656.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 21
    • 0000414496 scopus 로고
    • Reviews: a) O. Mitsunobu, Synthesis 1981, 1-28; b) D. L. Hughes, Org. Reac. 1992, 42, 335-656.
    • (1992) Org. Reac. , vol.42 , pp. 335-656
    • Hughes, D.L.1
  • 27
    • 0642380037 scopus 로고    scopus 로고
    • At this stage no air-oxidation products, such as disulfides, were detected. Nevertheless, purification of 2a by column chromatography on silica gel furnished the oxidized disulfide 3a as a side product (10% yield)
    • At this stage no air-oxidation products, such as disulfides, were detected. Nevertheless, purification of 2a by column chromatography on silica gel furnished the oxidized disulfide 3a as a side product (10% yield).
  • 33
    • 33751157324 scopus 로고
    • This latter yield was not improved with 2,2′-dithiobis(benzothiazole), which was recently reported to produce disulfides under mild conditions: E. Brzezinska, A. E. Ternay Jr., J. Org. Chem. 1994, 59, 8239-8244.
    • (1994) J. Org. Chem. , vol.59 , pp. 8239-8244
    • Brzezinska, E.1    Ternay Jr., A.E.2
  • 35
    • 0642288299 scopus 로고    scopus 로고
    • An irreversible oxidation peak that can be assigned to the formation of the S-S bond is observed near 2.4 V. Nevertheless, all attempts to convert 2a into 3a electrochemically were unsuccessful
    • An irreversible oxidation peak that can be assigned to the formation of the S-S bond is observed near 2.4 V. Nevertheless, all attempts to convert 2a into 3a electrochemically were unsuccessful.
  • 38
    • 0004918021 scopus 로고
    • That is in accordance with previous observations on related TTF derivatives: a) C. Livage, M. Fourmigué, P. Batail, E. Canadell, C. Coulon, Bull. Soc. Chim. Fr. 1993, 130, 761-771; b) K. A. Abboud, M. B. Clavenger, G. F. de Oliveira, D. R. Talham, J. Chem. Soc. Chem. Commun. 1993, 1560-1562; c) E. Ouahab, M. Fettouhi, J. F. Halet, V. M. Yartsev, C. Garrigou-Lagrange, P. Delhaes, C. Sourisseau, New J. Chem. 1993, 17, 399-408.
    • (1993) Bull. Soc. Chim. Fr. , vol.130 , pp. 761-771
    • Livage, C.1    Fourmigué, M.2    Batail, P.3    Canadell, E.4    Coulon, C.5
  • 39
    • 37049070533 scopus 로고
    • That is in accordance with previous observations on related TTF derivatives: a) C. Livage, M. Fourmigué, P. Batail, E. Canadell, C. Coulon, Bull. Soc. Chim. Fr. 1993, 130, 761-771; b) K. A. Abboud, M. B. Clavenger, G. F. de Oliveira, D. R. Talham, J. Chem. Soc. Chem. Commun. 1993, 1560-1562; c) E. Ouahab, M. Fettouhi, J. F. Halet, V. M. Yartsev, C. Garrigou-Lagrange, P. Delhaes, C. Sourisseau, New J. Chem. 1993, 17, 399-408.
    • (1993) J. Chem. Soc. Chem. Commun. , pp. 1560-1562
    • Abboud, K.A.1    Clavenger, M.B.2    De Oliveira, G.F.3    Talham, D.R.4
  • 40
    • 0013017393 scopus 로고
    • That is in accordance with previous observations on related TTF derivatives: a) C. Livage, M. Fourmigué, P. Batail, E. Canadell, C. Coulon, Bull. Soc. Chim. Fr. 1993, 130, 761-771; b) K. A. Abboud, M. B. Clavenger, G. F. de Oliveira, D. R. Talham, J. Chem. Soc. Chem. Commun. 1993, 1560-1562; c) E. Ouahab, M. Fettouhi, J. F. Halet, V. M. Yartsev, C. Garrigou-Lagrange, P. Delhaes, C. Sourisseau, New J. Chem. 1993, 17, 399-408.
    • (1993) New J. Chem. , vol.17 , pp. 399-408
    • Ouahab, E.1    Fettouhi, M.2    Halet, J.F.3    Yartsev, V.M.4    Garrigou-Lagrange, C.5    Delhaes, P.6    Sourisseau, C.7
  • 41
    • 33847088555 scopus 로고
    • 0.77: B. A. Scott, S. J. La Placa, J. B. Torrance, B. D. Silverman, B. Welber, J. Am. Chem. Soc. 1977, 99, 6631-6639. In addition to the very low values of the S1 and S2 coefficients, one can consider an overall cancelation of the bonding and antibonding interactions between orthogonal, neighboring TTFs.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 6631-6639
    • Scott, B.A.1    La Placa, S.J.2    Torrance, J.B.3    Silverman, B.D.4    Welber, B.5


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