Cyclopentane Hydrogen bromide

NBS can also be used to brominate alkanes. For example, cyclopropane, cyclopentane, and cyclohexane give the corresponding bromides when irradiated in a solution of NBS in dichloromethane. Under these conditions, the succinimidyl radical appears to be involved as the hydrogen-abstracting intermediate ... 

A surprisingly different approach was followed for obtaining both enantiomers of l,2-bis(di-phenylphosphino)cyclopentane 26. a ligand used in catalytic hydrogenations (Section D.2.5.1.2.1.1.) and hydrosilylation (Section D.9.). The racemic product was prepared by the reaction of cyclopentene with white phosphorus and phosphorus trichloride at elevated temperatures, followed by treatment with phenylmagnesium bromide. The racemate formed a complex with nickel(II) bromide which undergoes a Pasteur-type spontaneous resolution on crystallization from dichloromethane. The crystals were separated by hand27. 

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