N,N-dimethylformamide-mediated sodium reduction of frans-3,3′- benzo[c]thienylidene-1,1′ dithione and frans-3,3′-benzo[c] selenonylidene-1,1′-dithione

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3039-3041

  Aqad, Emad ^a,b   Lakshmikantham, M V ^a   Cava, Michael P ^a  

^a UNIVERSITY OF ALABAMA   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; N,N DIMETHYLFORMAMIDE; NAPHTHALENE DERIVATIVE; SODIUM; THIOKETONE;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 4544221373     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049205t     Document Type: Article

References (17)

1. Lakshmikantham, M. V.; Carroll, P.; Furst, G.; Levinson, M. I.; Cava, M. P. J. Am. Chem. Soc. 1984, 104, 6084.
2. Raasch, M. S.; Huang, N. Z.; Lakshmikantham, M. V.; Cava, M. P. J. Org. Chem. 1988, 53, 891.
3. Cava, M. P.; Lakshmikantham, M. V. Phosphorus, Sulfur, Silicon 1989, 43, 95.
4. Lakshmikantham, M. V.; Chen, W.; Cava, M. P. J. Org. Chem. 1989 54, 4746.
5. Lakshmikantham, M. V.; Aqad, E.; Rajagopal, D.; Cava, M. P. Phosphorus, Sulfur, Silicon 2004, in press.
6. Raasch, M. S.; Lakshmikantham, M. V.; Cava, M. P. Unpublished results.
7. Paulussen, H.; Haitjema, H.; van Asselt, R.; Mylle, P.; Adriaensens, P.; Vanderzande, D. Polymer 2000, 41, 3121.
8. Bergman, J.; Engman, L. Org. Prepr. Proc. Int. 1978, 10, 289.
9. (a) Simonet, J. In The chemistry of Functional Groups, Supplement S: The Chemistry of Sulfur-Containing Functional Groups; Patai, S., Rappaport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1993; Chapter 10, p 439.
10. (b) Yasui, S.; Nakamora, K.; Ohno, A.; Oka, S. Bull Chem. Soc. Jpn., 1982, 55, 1981.
11. Steimecke, G.; Sieler, H.-J.; Kirms, R.; Hoyer, E. Phosphorus, Sulfur, Silicon 1979, 7, 49.
12. 2: C, 47.79; H, 3.12; S, 14.18. Found: C, 47.71; H, 3.14; S, 14.29.
13. Quattrocchi, C.; Lazzaroni, R.; Bredas, J. L.; Kiebooms, R.; Vanderzande, D.; Gelan, J.; Van. Meervelt, L. J. Phys. Chem. 1995, 99, 3932.
14. Kwon, O.; McKee, M. L. J. Phys. Chem, 2000, 104, 7106.
15. To the best of our knowledge, the only known derivatives of biisothianaphthenes are tert-butyldimethylsilyl-capped biisothianaphthene, which was reported by us: (a) Okuda, Y.; Lakshmikantham, M. V.; Cava, M. P. J. Org. Chem. 1991, 56, 6024. The formyl-capped biisothianaphthene, which was reported recently: (b) Shimizu, Y.; Shen, Z.; Ito, S.; Uno, H.; Daub, J.; Ono, N. Tetrahedron Lett. 2002, 43, 8485.
16. To the best of our knowledge, the only known derivatives of biisothianaphthenes are tert-butyldimethylsilyl-capped biisothianaphthene, which was reported by us: (a) Okuda, Y.; Lakshmikantham, M. V.; Cava, M. P. J. Org. Chem. 1991, 56, 6024. The formyl-capped biisothianaphthene, which was reported recently: (b) Shimizu, Y.; Shen, Z.; Ito, S.; Uno, H.; Daub, J.; Ono, N. Tetrahedron Lett. 2002, 43, 8485.
17. Interestingly enough, the only patent describing the preparation of conductive poly-benzo[c]selenophene was reported in 1991 but was not further examined: Kubota, F. JP application no. 1989-86323; Chem. Abstr. 1991, 115, 2029.