7) For convenience these compounds will be referred to as K a r y l -K methylbenzamides containing "aza', "aza oxide", and "methyiazonium" substituents, respectively. (8) M. Liveris and T'he Reformatsky reaction between ethyl bromoacetate and l-acetoxy-4-phthalimido~2-butanone (4) produces in rnodest yield ~-acetoxy-~-(2-phthalimidoethyl)butyrolactone (10). a product of normal addition to the ketone carbonyl, and in low yield a second compound, which arises from transformation of the phthalimide group. The latter product is shown to be 1,5,8-trioxobenz~]indolizidine (13), a material which is of synthetic interest because of its *jtructural relationship to the phenanthroindolizidine and Amaryllidaceae alkaloids. The precursor to ketone 4, l-diazo-4-phthalimido-2-butanone (7), was found to give 13 directly in preparatively acceptable yield via a novel rearrangement of its derived ketocarbene (17).We are presently investigating a synthetic approach to the ring system of cocculolidine ( 1),2 a member of the D-ring lactone subgroup of the Erythrina group of alkaloids. This approach requires the as yet unknown aminobutenolide 2, and our immediate synthetic goal was the amine-protected lactone 3.T was and n 1 2 , R = H 3, R = o-phthaloyl e key step in an initial sequence designed to produce 3 he Reformatsky reaction between ethyl bromoacetate -acetoxy-4-phthalimido-2-butanone (4). This ketone was 4, Z = CH,OA.c 7 , Z == CHN, 5 , Z = OH 8, Z = CH,OCHO 6 , Z = C1 9, Z = CH,Cl readily prepared in four steps from /3-alanine (3-aminopropionic acid) via intermediates 5 , 6 , and 7, respectively.The major product of the Reformatsky reaction was the acetoxylactone 10, which was formed in modest yield (20%) and presumalily arose from normal addition to the ketone followed by transesterification and cyclization. This reaction also produced a second, highly colored, product "A" in lower 10, Y = OAc 11, Y = OCHO 12, Y =
