86156-85-6Relevant academic research and scientific papers
Studies on the Occurence of Hydrogen Transfer, 68. The Reductive Conversion of Aromatic Acyl Chlorides into Diarylacetylenes with Lithium Amalgam in a One-Pot Technique
Horner, Leopold,Dickerhof, Karlheinz
, p. 1615 - 1622 (2007/10/02)
Enediol diesters A obtained according to equation (1) by "acylating reductive dimerization" with lithium amalgam (Li/Hg) are transformed into acetylene derivatives by "reductive elimination" according to equation (2) using two more reduction equivalents.Preparatively, the "one pot technique" using the two step procedure is advantageous, cis- and trans-enediol diesters can also be reduced in good yields to acetylene derivatives by "reductive elimination" with sodium amalgam (Na/Hg) or potassium amalgam (K/Hg) according equation (2).An important condition for a successful reaction (2) is the direct linkage of two aromatic ligands to the C=C double bond.Enediol diesters with aliphatic ligands at the C=C double bond are stable to Li/Hg because of the potential involved.A reaction mechanism is presented in accordance with the half-wave potentials of all compounds paticipating in the reactions (1) and (2).
