Arenium acid catalyzed deuteration of aromatic hydrocarbons
The arenium acid [mesitylene-H]+ has been shown to be an extraordinarily active H/D exchange catalyst for the perdeuteration of polycyclic aromatic hydrocarbons. The reactions take place under ambient conditions in C6D6 as an inexpensive deuterium source. High isolated yields and excellent degrees of deuterium incorporation were achieved using the substrates p-terphenyl, fluoranthene, pyrene, triphenylene, and corannulene.
Duttwyler, Simon,Butterfield, Anna M.,Siegel, Jay S.
p. 2134 - 2138
(2013/04/10)
Rapid, microwave-assisted perdeuteration of polycyclic aromatic hydrocarbons
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.
Greene, Allison K.,Scott, Lawrence T.
p. 2139 - 2143
(2013/04/10)
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