ChemInform Abstract: PHOTOREACTIONS OF NONBASIC PHTHALIMIDE DERIVATIVES

Abstract

Während (Ia) bei der Photolyse in THF die Produkte (IIa), (IIIa) und (IVa) ergibt, wird aus (Ib) das Derivat (IIIb) erhalten, (IIIb) reagiert in der Hitze oder in Anwesenheit von HBr zu (V).

Phthalimide and Its Derivatives

“…(1,8) In the same way, both N-methyl-and N-ethyl-phthalimide can be photoreduced with methanol or ethanol to give(9) the corresponding 3-hydroxyisoindolinone and a similar amount of photoaddition product [equation (3) A report(tO) of the use of amines as hydrogen donors shows that under some conditions the pattern of products includes the dimeric photoreduced imide as well as the monomeric reduction product and the photoadduct [equation (4)]. An unusual feature of the reaction with amines is that triethylamine, and also N,N-dimethylcyclohexylamine in one experiment, gives the further reduced product 2-methylisoindolinone [equation (5)], although there is no comment on the factors that promote this type of photoreduction.…”

“…A number of phthalimides have been studied with substituents other than simple alkyl groups on the nitrogen. N-(MethoxymethyI)phthalimide and N(carboxymethyI)phthalimide give photoaddition products with tetrahydrofuran, (5) but the only product isolated from the irradiation of thalidomide is the substituted 3-hydroxyisoindolinone [equation (8)]. A series of N-methylenebisphthalimides showed o t) that, with a suitable length of bridging group, the intramolecular pinacol-like product predominates over products in which one or both of the imide groups is separately reduced [equation (9)].…”