The reaction of β-amino alcohols with triphenylphosphine dibromide was found to give the corresponding aziridines in good yields. The reaction opened a new route to the synthesis of aziridine compounds which seems to be more convenient than the Gabriel and Wenker methods. In the ring closure of ephedrine, a Walden inversion was observed. A possible mechanism is suggested.
Disubstituted aminotriphenylphosphonium bromides were obtained in excellent yields from the reaction of triphenylphosphine dibromide and the secondary amines using simple procedures. This method has an advantage in the preparation of cyclic aminophosphonium salts, such as those of morpholine or piperidine. The treatment of the disubstituted aminophosphonium salt with bases resulted in dehydrohalogenation, followed by a Hofmann-like decomposition, and gave imine and triphenylphosphine.
When aziridines (1) were treated with acetyl compounds, such as acetyl chloride, acetic acid, acetic anhydride, and thioacetic acid, the corresponding acetamide derivatives were obtained in good yields. In the case of acetyl chloride, some derivatives of N-(2-chloroethyl)acetamide (5) were found to be unstable in the face of moisture; they were easily hydrolyzed to give N-(2-hydroxyethyl) acetamide hydrochlorides (3). The NMR spectrum of N-(2-mercaptoethyl)-N-benzylacetamide (12) was discussed.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.