mixture was poured into ice-water(l00 ml) and extracted with CHC13(100 ml x 3). The extract was washed with H20, dried over MgS04 and evaporated to give Z-methylpropyl phenyl ketone(5d) as an oil(l6.20 g, 94%). 'H-NMR: 8.00(2H,dd,J=8.5 and 1.5Hz1, 7.60-7.23 (3H,m), 2.84(2H,d, J=6.8Hz), 2.40-2.08(lH,m), 1.00(6H,d,J=6.6Hz). IR(KElr): 1686(C=O). MS (m/zl(M+):Calcd for Cl,H140: 162.1042. Found:l62.1042. Reaction of 2-methylpropyl phenyl ketone(5d)(2.00 g, 12.3 mm011 obtained as above with BTMA Br3t7.21 g, 18.5 nznol) in CH2C12-MeOH(5:21(56 ml) gave 3d as an oil(1.95 g, 66 %I. 'H-NMR: 8.00(2H,dd,J=B.5 and 1.5H.z), 7.65-7.26(3H,m), 4.94(1H,d,J=8.5Hz), 2.57-2.36 (lH, ml, 1.22, l.O3(each 3H,d,J=6.6Hz). IR(KBr): 1679(C=O). MS(m/z)(M+): Calcd for Cl,H13Br0:240.0148. Found:240.0118. c+Phenylphenacyl Bromide(3e) Reaction of deoxybenzoin(5e)(5.32 g, 27.1 mm011 with BTMA Br3(15.85 g, 40.7 mm011 in CH2C12-MeOH(5:2)(84 ml) gave 3e as an oil(6.41 g, 98%). 'H-NMR: 7.99(2H,dd,J=8.5 and 1.5Hz1, 7.66-7.26(8H,m), 6.38(lH,s). IR(KBr):l687(C=O). FABMS(m/z) (M+H):Calcd for C14H,2Br0:275.0072. Found:275.0069. N-(2-Iodobenzyl)-a,N-dimethylphenacylamine(2b) A solution of the phenacyl bromide(3b) (1.70 g. 7.98 mm011 in dioxane(25 ml) was added to a solution of the benzylamine(4)(4.17 g, 16.9 nznol) in dioxane(25 ml). The mixture was stirred for 18 h at 55-6O'C. The precipitates formed were filtered and the filtrate was evaporated to give a crude oil(4.60 g). This was subjected to flash chromatography on Si02 with benzene-hexane(l:l) to give 2b as a pale yellow oil(2.51 g, 82%). 'H-NMR: 7.92(2H,dd,J=8.5 and 1.5Hzi, 7.82(1H,d,J=7.6HzI,