Abstract
Ring formation via an intramolecular Grignard coupling reaction of trihaloalkanes is presented. 2-Methyl-2-(chloromethyl)-l,5-dichloropentane was prepared and treated with two equivalents of magnesium in tetrahydrofuran, to study the possible ring formation through 1,5 and/or 1,3 coupling reactions. A 1,3 Grignard coupling reaction was shown to occur preferentially, and a cyclopropane derivative was formed. A 1,5 coupling reaction could not be realized under the prevailing reaction conditions. A diradical mechanism for the Grignard coupling reaction is proposed to account for the behavior of this compound and other similar polymetallophilic systems in their reaction with magnesium.
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