The first Diels-Alder reaction of a 9,10-bis(1,3-dithiol-2-ylidene)- 9,10-dihydroanthracene derivative: Synthesis and crystal structure of a novel donor-π-anthraquinone diad

Chemical Communications

Volumn , Issue 23, 1999, Pages 2433-2434

  Christensen, Christian A ^a   Bryce, Martin R ^a   Batsanov, Andrei S ^a   Howard, Judith A K ^a   Jeppesen, Jan O ^b   Becher, Jan ^b  

^a DURHAM UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRAQUINONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; POTENTIOMETRY; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0033534073     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907768e     Document Type: Article

References (26)

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21. Reagent 5 was prepared from zinc bis[2-thioxo-1,3-dithiole-4,5-bis-(thiolate)] (C. Wang, A. S. Batsanov, M. R. Bryce and J. A. K. Howard, Synthesis, 1998, 1615) by the same methods used previously for close analogues [ref. 5(a)].
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23. R. M. Renner and G. R. Burns, Tetrahedron Lett., 1994, 35, 269; Similar reactions afford 4-formyl-5-methyl-4′,5′-bis(methylsulfanyl)TTF and 4,5-bis(2-cyanoethylsulfanyl)-4′-formyl-5-methyl-TTF (ca. 40% yields) ( J. O. Jeppesen and J. Becher, unpublished results). The former reaction was also observed (25% yield) by P. Blanchard, PhD Thesis, Université de Nantes, 1994. A very different mechanism from Scheme 2 was postulated.
24. R. M. Renner and G. R. Burns, Tetrahedron Lett., 1994, 35, 269; Similar reactions afford 4-formyl-5-methyl-4′,5′-bis(methylsulfanyl)TTF and 4,5-bis(2-cyanoethylsulfanyl)-4′-formyl-5-methyl-TTF (ca. 40% yields) ( J. O. Jeppesen and J. Becher, unpublished results). The former reaction was also observed (25% yield) by P. Blanchard, PhD Thesis, Université de Nantes, 1994. A very different mechanism from Scheme 2 was postulated.
25. Other workers have observed the formation of bis(oxydimethylene)-TTF when chlorinating tetrakis(hydroxymethyl)-TTF [ref. 7(c) and S. Hsu and L. Chiang, Synth. Met., 1988, 27, B651].
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