4-METHOXY-1-METHYLPYRIDINIUM IODIDE . STEVENS REARRANGEMENT OF BOROHYDRIDE REDUCTION PRODUCT

Stevens rearrangement of 4-methoxy-1-p-methoxybenzyl-1-methyl-1,2,5,6-tetrahydropyridinium chloride (3) monohydrate, prepared from 4-methoxy-1-methylpyridinium iodide (1), has given ring-fission products, pmethoxybenzy 1-N-methylamine (4), 3-methoxy-5-(N-p-methoxybenzyl-N-methyl)amino-1,3-pentadiene (5), and 5-(N-p-methoxybenzyl-N-methyl)amino-3-phenyl-1-penten-3-ol (9), in addition to 4-p-methoxybenzyl-lmethyl- 2-phenyl-l,2,5,6-tetrahydropyridine (8) (a 1,4-rearrangement-addition product) and the desired 4-methoxy-2-p-methoxybenzyl-1-methyl-1,2,5,6-tetrahydropyridine (6). The nmr spectral properties of 6 were intimately compared with those of the corresponding 4 isomer (10). © 1969, American Chemical Society. All rights reserved.