265 1 isooctane/ether, 1/1, to give 5.8 g (47%) of 2,3-diethylmaleimide: mp 69-70 "C (lit.47 mp 68 O C , lit.48 mp 68-70 "C); R, (GC) 3.30 min.cis -3,4-Diethylpyrrolidine-2,5-dione (cis -2,3-Diethylsuccinimide). To 180 mg (0.85 mmol) of the above 3,4-diethyl-lH-pyrrole-2,5-dione in 10 mL of ethyl acetate was added 18 mg of PtO,. Hydrogen at 50 psi was applied for 6 h,?! the solution was filtered through Celite, and the filtrate was evaporated to give 132 mg (100%) of residue. GC analysis showed a 95/5 mixture of cis/trans isomers which may be due to epimerization during analysis, as the cis compound was never found completely free of the trans by GC analysi~.~" The product was recrystallized from M e O H / H 2 0 and sublimed at 70 OC/l torr to give a 98/2 ratio of &/trans 2,3-diethylsuccinimide as white crystals: mp 87-89 "C; R, (GC) cis 5.16 min, trans 4.17 min; UV A , , , (log e) 246 (1.93), 221 nm (2.28); IR (KBr) 3130, 1670, 1340 cm-'; NMR (CDCI,, 90 MHz) 6 1.02 (t, 6 H, 2 X CH2CH3, J = 7.5 Hz), 1.54-1.77 (m, 4 H, 2 X CHICH3), 2.70-2.83 (m, 2 H, 2 X CH), 8.32Abstract: p-Nitrophenyl acetate, p-nitrophenyl hexanoate, and p-nitrophenyl diphenyl phosphate (PNPDPP) were cleaved by o-iodosobenzoate, o-iodoxybenzoate, and 5-(n-octyloxy)-2-iodosobenzoate (3) in aqueous micellar cetyltrimethylammonium chloride solutions at pH 8. The system 3/CTACI was the best catalyst and P N P D P P was the most reactive substrate. In a remarkably rapid hydrolytic reaction a t 25 OC, 1.0 X
