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Metallopinacolate Intermediates in the Reductive Coupling of Acetone Promoted by Uranium Reagents
Author(s) -
Maury Olivier,
Villiers Claude,
Ephritikhine Michel
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199611291
Subject(s) - acetone , uranium , reagent , chemistry , counterion , lithium (medication) , amalgam (chemistry) , coupling reaction , inorganic chemistry , organic chemistry , catalysis , ion , materials science , medicine , electrode , metallurgy , endocrinology
New aspects of the mechanism of the McMurry reaction were revealed by studying the coupling of acetone with uranium tetrachloride and lithium or sodium amalgam. The two metallopinacolate intermediates 1 and 2 were isolated. Only the cyclic complex 2 , formed by reaction of 1 with the reducing agent, was transformed, under more forcing conditions, into tetramethylethylene. Counterion: Li + .