4109-95-9Relevant articles and documents
Spectroscopic Characterization of Heterohalogenic Dihalomethylzinc Carbenoids: Application to a More Efficient Chlorocyclopropanation Reaction
Taillemaud, Sylvain,Charette, André B.
supporting information, p. 83 - 92 (2022/01/04)
Dihalomethylmetal reagents are important species that can be used in halocyclopropanation reactions (metal = zinc) as well as in alkenyl halide synthesis. When trihalomethanes containing two or more different halogen atoms are used to prepare zinc carbenoids, several species can be formed through a halogen scrambling process. This affects which halocyclopropane, or haloalkene, is generated in the subsequent reaction. In the first part of the paper, we report an extensive characterization of zinc dihalocarbenoids by NMR to identify the major species formed when various di-and trihalomethane reagents are used as carbenoid precursors. In the second part of the paper, a direct application of this information enabled the development of a highly efficient chlorocyclopropanation reaction of allylic alcohols from inexpensive and accessible precursors.
