Radical cation Diels-Alder reaction between indoles and exocyclic 1,3-dienes with incorporated intentional cleaving points

Chemical Communications

Volumn , Issue 5, 1999, Pages 433-434

  Peglow, Thomas ^a   Blechert, Siegfried ^a   Steckhan, Eberhard ^b  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDROCARBAZOLE DERIVATIVE; ALKADIENE; CATION; EXOCYCLIC DOUBLE BOND; INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; ELECTRON TRANSPORT; LIGHT; ORGANIC CHEMISTRY;

EID: 0033531417     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900078j     Document Type: Article

References (29)

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24. It has been previously shown that for an efficient radical cation Diels-Alder reaction, the oxidation potentials, which correspond to the HOMO energies, of diene and dienophile should not differ by much more than 500 mV; a smaller difference normally results in higher yields; J. Mlcoch and E. Steckhan, Angew. Chem., 1985, 97, 429; J. Mlcoch and E. Steckhan, Tetrahedron Lett., 1987, 28, 1081; M. Martiny, E. Steckhan and T. Esch, Chem Ber., 1993, 126, 1671.
25. It has been previously shown that for an efficient radical cation Diels-Alder reaction, the oxidation potentials, which correspond to the HOMO energies, of diene and dienophile should not differ by much more than 500 mV; a smaller difference normally results in higher yields; J. Mlcoch and E. Steckhan, Angew. Chem., 1985, 97, 429; J. Mlcoch and E. Steckhan, Tetrahedron Lett., 1987, 28, 1081; M. Martiny, E. Steckhan and T. Esch, Chem Ber., 1993, 126, 1671.
26. It has been previously shown that for an efficient radical cation Diels-Alder reaction, the oxidation potentials, which correspond to the HOMO energies, of diene and dienophile should not differ by much more than 500 mV; a smaller difference normally results in higher yields; J. Mlcoch and E. Steckhan, Angew. Chem., 1985, 97, 429; J. Mlcoch and E. Steckhan, Tetrahedron Lett., 1987, 28, 1081; M. Martiny, E. Steckhan and T. Esch, Chem Ber., 1993, 126, 1671.
27. Prepared via a Heck reaction analogous to dienes 5.
28. S. Blechert and E. Steckhan, unpublished results.
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