“…Consequently, path b of Scheme I represents an important competing reaction sequence that leads to the production of unwanted products and reduced yields of 2. This sequence is similar to the Fujiwara reaction, in which CHCl3 reacts with pyridine in a solution of alkaline hydroxide.11 The major products of the Fujiwara reaction are aldehydic imines and amidines derived from cleavage of the Nalkylated pyridine ring.12 This reaction is performed under conditions consistent with the production of :CC12 and is inhibited with common carbene traps such as methanol.13 Although the Fujiwara reaction is generally executed in single-phase media, other reactions have reportedly been performed under conditions of basic PTC with CHClJ and substituted pyridines that invoke mechanisms involving the reaction of :CC12 at the pyridyl ring nitrogen.14 Moreover, various other carbenes (e.g., : C (CN) 2 and : C (C02Et) 2) are known to form stable ylides with pyridine and azanaphthalenes,6,15 and recently it has been reported that ylide intermediates are formed by the reaction of pyridine with phenylchlorocarbene ,16 In the case of 2-AMP, an analogous reaction is proposed in which the pyridyl ring nitrogen competes with the aminomethyl group for :CC12 to generate a -cc12-pyridinium species (8).…”