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A Vinylogous Donor in an Iron(III)‐Catalysed Michael Reaction and an Enone–Dienol Tautomerism
Author(s) -
Christoffers Jens
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199805)1998:5<759::aid-ejoc759>3.0.co;2-w
Subject(s) - tautomer , chemistry , enone , michael reaction , cycloalkene , reactivity (psychology) , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
A double acceptor‐activated cycloalkene 1 reacts in an FeCl 3 · 6 H 2 O catalysed Michael reaction surprisingly as a donor. The constitution of the product 2 results from a reaction of 1 in the γ‐position, thus the Michael reaction is vinylogous with respect to the donor. A tautomerism between the enone 1 and the dienol 4 is found to be a precondition for this reactivity.