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J Org Chem. 2013 Mar 1;78(5):2139-43. doi: 10.1021/jo301903m. Epub 2012 Nov 5.

Rapid, microwave-assisted perdeuteration of polycyclic aromatic hydrocarbons.

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1
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.

Abstract

A simple and convenient method for the perdeuteration of polycyclic aromatic hydrocarbons that does not require strong acid has been developed. Using commercially available reagents, the one-step procedure provides a new route to perdeuterated derivatives of both common and exotic polycyclic aromatic hydrocarbons. Microwave irradiation of the hydrocarbons in a solution of dimethylformamide-d7 containing potassium tert-butoxide affords rapid and essentially complete H/D exchange. For example, corannulene is converted to corannulene-d10 with >98% deuterium incorporation in just 1 h of microwave irradiation in a solution of t-BuOK/DMF-d7.

PMID:
23121393
DOI:
10.1021/jo301903m
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