137768-28-6Relevant articles and documents
Arene Hydrides, 10. Michael Additions of Anthracene Hydride. Selective Reduction of the ArC=C Moiety by Fragmentation of the Michael Adduct
Sommer, Andreas,Stamm, Helmut
, p. 99 - 102 (2007/10/02)
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-bicyclononanones" 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.Key Words: Cinnamic acid derivatives, selective saturation / Michael addition / Anthracene hydride