Nitrous oxide as a nucleophile in the formation of a new reactive intermediate from benzyl cations in the solvolysis of benzyl azoxytosylate
Abstract
Rate and product analytical results of solvolysis of benzyl azoxytosylate in 1 : 1 (v/v) trifluoroethanol: water require two product-forming routes: one involves a long-lived intermediate (formed from benzyl cations and nitrous oxide) which is trappable by dilute nucleophiles and bases; the other involves either a very short-lived intermediate (the benzyl cation) which is not capable of being intercepted by solutes, or no intermediate at all.