Synthesis of arylcalcium halides - General procedure, scope and limitations
A general procedure for the synthesis of a wide variety of arylcalcium halides by activation of the alkaline earth metal as well as bromo- or iodoarenes is reported. Chloro- and fluoroarenes are not suitable substrates for an insertion of calcium into the carbon-halogen bond. Furthermore, ortho-fluoro substitution prevents the formation of the corresponding heavy calcium organometallics. The ipso-carbon atoms show a strong low-field shift in the 13C NMR spectra. The arylcalcium iodides crystallize monomeric as tetrakis(THF) complexes. Naphthylcalcium iodide shows a Ca-C bond length of 255.2(6) pm which lies in the characteristic region. Georg Thieme Verlag Stuttgart.
A reinvestigation of the reaction of arylcalcium iodides with nitrous oxide
The previously reported reaction of phenylcalcium iodide with N2O in ether to form products with aryl-N bonds has been reexamined with various solvents and methylated aryliodides. The yield of azobenzene is maximized using DME as the solvent, and the insertion reactions may involve diorganocalcium (Ar2Ca) intermediates.
Hanusa, Timothy P.
p. 2435 - 2436
(2007/10/02)
A new method for preparation of organocalcium halides by cocondensation of calcium vapor with solvents
Calcium vapor (atom) when cocondensed with various solvents at 77 K was found to be very reactive toward alkyl and aryl halides.A series of organocalcium halides was prepared in good yields by addition of alkyl and aryl halides to the resultant calcium atom-solvent slurries at ambient temperatures.
Mochida, Kunio,Yamanishi, Takayuki
p. 247 - 252
(2007/10/02)
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