Pyrrolo annelated tetrathiafulvalenes: The parent systems

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1291-1294

  Jeppesen, Jan Oskar ^a   Takimiya, Kazuo ^a,b   Jensen, Frank ^a   Becher, Jan ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001364311     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9902428     Document Type: Article

References (40)

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29. 3 has been reported by Müllen and co-workers, see: Skabara, P. J.; Müllen, K.; Bryce, M. R.; Howard, J. A. K.; Batsanov, A. S. J. Mater. Chem. 1998, 8, 1719-1724.
30. 3 has been reported in a communication from Gorgues and co-workers, see: Durand, C.; Hudhomme, P.; Duguay, G.; Jubault, M.; Gorgues, A. Chem. Commun. 1998, 361-362.
31. Self-coupling of 13b using triethyl phosphite afforded bis(2,5-dihydro-N-tosylpyrrolo[3,4-d])tetrathiafulvalene in 35% yield. All attempts to remove the tosyl groups failed due to the chemical stability of the sulfamide bond.
32. Care must be taken during workup, especially with regard to temperature; otherwise ring opening occurs in the 1.3-dithiole ring and a mixture of 15 and 3,4-bis(methylthio)pyrrole is isolated.
33. The X-ray data and molecular structure are included as Supporting Information.
34. .+ with the B3LYP/6-31G(d) method and the PCM solvent model, using PM3-optimized geometries.
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