Formation and reactivity of 2-styryl-1,4-benzoquinones

European Journal of Organic Chemistry

Volumn , Issue 17, 2001, Pages 3307-3311

  Brehm, Isabella ^a   Meier, Herbert ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Cycloaddition; Oxidation; Polycycles; Quinones; Stilbenes

Indexed keywords

2 STYRYL 1,4 BENZOQUINONE DERIVATIVE; BENZOQUINONE DERIVATIVE; POLYCYCLIC AROMATIC COMPOUND; SILICA GEL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIMERIZATION; MOLECULAR INTERACTION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0034855627     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200109)2001:17<3307::AID-EJOC3307>3.0.CO;2-T     Document Type: Article

References (15)

1. R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440-1469;
2. Angew. Chem. Int. Ed. 1999, 38, 1350-1377.
3. U. Scherf, Topics Curr. Chem. 1999, 201, 162-222.
4. K. Müllen, G. Wegner, Electronic Materials: The Oligomer Approach, Wiley-VCH, Weinheim 1998.
5. W. R. Salaneck, I. Lundström, B. Rånby, Conjugated Polymers and Related Materials, Oxford University Press, Oxford 1993.
6. H. Meier, Angew. Chem. 1992, 104, 1425-1446;
7. Angew. Chem. Int. Ed. Engl. 1992, 31, 1399-1420.
8. H.-H. Hörhold, M. Helbig, D. Raabe, J. Opfermann, U. Schurf, R. Stockmann, D. Weiß, Z. Chem. 1987, 27, 126-137.
9. See, for example: M. Lehmann, B. Schartel, M. Hennecke, H. Meier, Tetrahedron 1999, 55, 13377-13394 and references therein.
10. 4]to the corresponding 1,4-benzoquinones was not successful here.
11. H. Irngartinger, B. Stadler, Eur. J. Org. Chem. 1998, 605-626.
12. [9] has to be changed.
13. AM1: Win MOPAC, version 2.0.1.
14. 4 in a yield of 16%. It turned out that the structure of the isomer is a complicated polycyclic system, in which all four carbonyl groups of 8a disappeared; the final proof for the structure will be given by an X-ray investigation.
15. H. Meier, R. Petermann, U. Dullweber, J. Prakt. Chem. 1998, 340, 744-754.