ChemInform Abstract: Steric Strain and Reactivity: Electrophilic Bromination of trans-(1-Methyl-2-adamantylidene)-1-methyladamantane.
Abstract
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ChemInform Abstract
UV-VIS and NMR spectroscopic investigation of the title compound (I)—bromine system in comparison with that of the unsubstituted parent compound, adamantylideneadamantane, shows a marked effect of the steric strain present in (I) on the reactivity of the double bond. At very low bromine concentration, compound (I) is rapidly transformed into rearranged substitution product (II), whereas at high bromine concentration, compound (I) generates a bromonium polybromide ion pair (III), which is stable and unable to further evolve into products.
