Functionalization of homodiamantane: oxygen insertion reactions without rearrangement with dimethyldioxirane.

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2014
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Abstract
Homodiamantane bromination and nitroxylation are accompanied by contraction of the seven-membered ring to give the corresponding substituted 1-diamantylmethyl derivatives. In contrast, CH-bond hydroxylations with dimethyldioxirane retain the cage and give both apically and medially substituted homodiamantanes. The product ratios are in accord with the barriers for the oxygen insertion computed with density functional theory methods only if solvation is included through a polarizable continuum model. B3LYP-D3 and M06-2X computations with a 6-31G(d,p) basis set on the oligomeric van der Waals complexes predict the potential of homodiamantane derivatives for surface modifications with conformationally slightly flexible diamondoid homologues.
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Authors Fokin, Andrey A;Zhuk, Tatyana S;Pashenko, Alexander E;Osipov, Valeriy V;Gunchenko, Pavel A;Serafin, Michael;Schreiner, Peter R;
Journal The Journal of organic chemistry
Year 2014
DOI
10.1021/jo4026594
URL
Keywords
photochemistry reactivity polyolefins diels–alder reactions bromination epoxidation hydrogenation

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