Edward L. McCaffery, S. Shalaby
Feb 1, 1965
Citations
0
Influential Citations
6
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract In an attempt to study polymetallophilic organic compounds for use in the synthesis of chemical intermediates and new macromolecular systems, 2-methyl-2-(chloromethyl)-1,3-dichloropropane was reacted with magnesium. The reaction consumed two moles of magnesium per mole of compound and was shown to have produced 3-methyl-3-butenylmagnesium chloride which resulted from a skeletal rearrangement during the formation of the Grignard reagent. Carbonation of the Grignard reagent produced 4-methyl-4-pentenoic acid. The organomagnesium compound was also reacted with phenyl isocyanate to produce the corresponding anilide, with water to obtain 2-methyl-1-butene and with benzonitrile to form 4-methyl-4-pentenophenone. All of these compounds with the exception of the olefin have never been characterized and were therefore prepared by an independent method. A mechanism for the rearrangement is proposed.