ISSN:
0170-2041
Keywords:
Cinnamic acid derivatives, selective saturation
;
Michael addition
;
Anthracene hydride
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Anthracene hydride (AH-) in THF undergoes Michael addition onto the acrylic acid derivatives 1 and 2. Secondary reactions of the first formed anions 3 and 4 of the Michael adducts depend on the absence (3) or presence (4) of an aryl group in β position. The non-benzylic 3 or its protonated or deprotonated form can cyclize via ester condensation to yield the “dibenzo-bicyclo[3.2.2.]nonanones” 10b, c. Deprotonation of the anion 4 by excess AH- usually leads to fragmentation of the C—CAr bond formed in the Michael addition. The overall result is a selective C = C reduction of cinnamonic acid derivatives and analogues: PhR′C = C → PhR′CH — CH. This fragmentation is hampered in the Michael addition adduct 4h with dimethyl benzylidenemalonate 2h probably due to the necessity of a pronounced conformational reorganization during the fragmentation step.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199219920120
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