The vinylogous Michael reaction - A novel perspective for biaryl synthesis

European Journal of Organic Chemistry

Volumn , Issue 10, 1999, Pages 2511-2514

  Christoffers, Jens ^a   Mann, Alexander ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Biaryls; Homogeneous catalysis; Iron; Michael additions; Quinones

Indexed keywords

BENZOQUINONE DERIVATIVE; FURAN DERIVATIVE; IRON; KETONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIMERIZATION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032821545     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199910)1999:10<2511::aid-ejoc2511>3.0.co;2-3     Document Type: Article

References (23)

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19. This oxidation is consistent with redox properties typical for quinones: The Chemistry of the Quinoid Compounds (Eds.: S. Patai, Z. Rapoport), Wiley, New York, 1988.
20. In contrast to 6c-6e, compounds 6a and 6b show an unexpected substitution pattern in the cyclohexanone ring which is connected at the β-position to the quinone system. We presume 6a and 6b to be the result of a side reaction of a [2+2]-cycloaddition followed by a retro-Michael reaction.
21. As other by-products we were able to identify charge-transfer complexes. Moreover, we presume formation of radical coupling by-products which, however, we have not been able to detect as yet.
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