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Reactivity of [1(2,3)4]pentamantane (Td-pentamantane): a nanoscale model of diamond.
- Source :
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The Journal of organic chemistry [J Org Chem] 2006 Oct 27; Vol. 71 (22), pp. 8532-40. - Publication Year :
- 2006
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Abstract
- To model the chemical properties of the hydrogen-terminated nanodiamond {111} and {110} surfaces, the functionalizations of the higher diamondoid [1(2,3)4]pentamantane were studied. [1(2,3)4]Pentamantane reacts selectively with neat bromine to give the medial 2-mono- and 2,4-disubstitution products. In contrast, oxidation with nitric acid as well as single-electron-transfer oxidation involving the [1(2,3)4]pentamantane radical cation results in apical C7-substitutions. This substitution pattern dominates in the free-radical bromination under phase-transfer catalytic conditions that gives a mixture of 7- and 2-bromo[1(2,3)4]pentamantane in a 95:5 ratio. Replacement of the functional groups in [1(2,3)4]pentamantane occurs without isomerization. This was demonstrated for the interconversions of the bromo and hydroxy derivatives as well as for the preparation of [1(2,3)4]pentamantyl-7-thiol from 7-hydroxy[1(2,3)4]pentamantane. Thus, the selective functionalization of hydrogen-terminated nanodiamonds is possible by means of reactions with common electrophiles-oxidizers.
Details
- Language :
- English
- ISSN :
- 0022-3263
- Volume :
- 71
- Issue :
- 22
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 17064030
- Full Text :
- https://doi.org/10.1021/jo061561x