Collect. Czech. Chem. Commun. 2008, 73, 811-821

On the C-C Coupling of the Naphthylium Ion with Methane

Jana Roithováa,b, Claire L. Rickettsa,c and Detlef Schrödera,*

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
b Department of Organic Chemistry, Charles University, Hlavova 8, 128 43 Prague 2, Czech Republic
c Space Science Division, NASA Ames Research Center, Mail stop 245-6, Moffett Field, CA 94035, U.S.A.


Unlike other medium-sized hydrocarbon cations CmHn+ (m = 7-11, n = 6-12), the naphthylium ion C10H7+ undergoes a thermal reaction with methane to form the C-C coupled product C11H9+ concomitant with dehydrogenation. This reaction, which might be of relevance in the context of the growth of hydrocarbon species under extreme conditions, is suggested to lead to a benzylium-type cation in analogy to the C-C coupling of phenyl cations with methane.

Keywords: Benzotropylium; C–C coupling; Mass spectrometry; Methane activation; Naphthylium ion.

References: 52 live references.