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New Reagents, XXXIV. (Diphenylarsino)methyllithium: Synthesis and Preparative Applications
Kauffmann, Thomas,Altepeter, Bruno,Klas, Norbert,Kriegesmann, Reinhard
, p. 2353 - 2364 (2007/10/02)
(Diphenylarsino)methyl iodide (3) was synthesized for the first time (76 percent). (Diphenylarsino)methyllithium (2), stable at 20 deg C, is accessible from 3 (ca. 100 percent) by iodine-lithium exchange with butyl- or phenyllithium and by organoelement-lithium exchange with butyllithium from diphenylarsane (4d; 92 percent). 2, prepared from 4d, gives far better yields of (diphenylarsino)alkanes by the reaction with alkyl halides than 2, obtained from 3.To the contrary, no difference is observed in the reactivity of 2 from 3 or 4d towards aldehydes and ketones.
