Iron catalysis of Grignard reductions. Mechanism of 1,3-reductive eliminations from γ-propyl halides was written by Rollick, K. L.;Nugent, W. A.;Kochi, J. K.. And the article was included in Journal of Organometallic Chemistry in 1982.Electric Literature of C7H15BrO This article mentions the following:
The Fe3+-catalyzed reduction of 3-substituted propyl bromides by Grignard reagents gives propylene (I) and cyclopropane. The reduction to I is particularly noteworthy since it formally represents a 1,2-H shift. Two key intermediates are identified in I formation, in which MeO(CH2)3Br is first catalytically reduced to the Mg derivative by the Grignard reagent. The Fe3+-catalyzed β-elimination of the MeO(CH2)3MgBr intermediate gives CH2:CHCH2OMe, which is then reductively cleaved to I. Extensive studies of D labeling in the reactants, as well as in both intermediates, allow the course of the H shift to be followed unequivocally. The mechanism of Fe catalysis is proposed for the first and second stages of the reduction to I. In the experiment, the researchers used many compounds, for example, 1-Bromo-6-methoxyhexane (cas: 50592-87-5Electric Literature of C7H15BrO).
1-Bromo-6-methoxyhexane (cas: 50592-87-5) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Electric Literature of C7H15BrO
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary