有機固相反応の研究 : 固相Gabriel反応

抄録

The Gabriel reaction in the solid state was studied and found to proceed in high yield. In the solid-state reactions of potassium phthalimide (1) with p-bromophenacyl bromide (2), 2-bromoacetylnaphthalene (3), and p-nitrobenzyl bromide (4), the corresponding N-derivatives, i.e., N-(4-bromophenacyl) phthalimide (7), N-(2-naphthoylmethyl) phthalimide (8), and N-(p-nitrobenzyl) phthalimide (9), were obtained in yields of 96.2%, 99.6%, and 90.1%, respectively. The change of the halogen in a series of p-nitrobenzyl halides showed that the reactivity was in the order of Br>Cl>I. The cleavage of carbonhalogen bonds in the solid-state Gabriel reaction is affected by the ready cleavage of organic halides, the extent of contact between reactants due to grinding, and the activated state produced by a reaction temperature and a mechanical energy such as grinding.