Trimethylchlorosilane-modified Clemmensen reduction of metallocenyl ketones: trapping and X-ray structures f aliphatic, olefinic, silylated pinacolic, and rearranged pinacolonic products

The McMurry Coupling and Related Reactions

“…It is very interesting to note that the same orthocyclophane 87 was obtained in 91% yield by treating its dicarbonyl precursor with Zn(Hg) and HCl in place of the TiCl 3 -LiAlH 4 system [121]. Moreover, the chlorosilane-modified Clemmensen reduction has, in some cases, proved to be a useful alternative to the McMurry alkene synthesis, in particular with electron-rich aromatic carbonyl compounds and metallocenic ketones [297]. These marked similarities between the McMurry and Clemmensen reactions may reflect the involvement of similarly reactive carbenoid species in the two reactions.…”

Synthesis of arylferrocenylketones

“…5a Bildstein and co-workers reported the synthesis of olefin-containing ferrocene derivatives from the corresponding ketones for modeling purposes of molecular electronic devices. 6 Such olefins have also been used in the synthesis of polymers that are used as coating materials for aerospace applications. 7 Despite their importance, to the best of our knowledge, just a few ferrocenylmonoketones have been prepared using the Friedel-Crafts reaction, which greatly limits the functional groups that can be attached to the carbonyl group (i.e., the nitrophenyl group).…”

The McMurry Coupling and Related Reactions

“…A very low concentration of HCl must be present to obtain satisfactory results. 92 Zinc dust in combination with the acidic ionic liquid 1-butyl-3-methylimidazolium chloroaluminate converts aromatic aldehydes and ketones to alkenes with (Z)-stereoselectivity. 46 Zirconium Reagents.…”