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

Abstract

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.