104144-02-7Relevant articles and documents
Utilization of Phenylthio Substituted Amines for the Synthesis of Pyrrolidines
Padwa, Albert,Dent, William,Nimmesgern, Hildegard,Venkatramanan, M. K.,Wong, George S. K.
, p. 813 - 828 (2007/10/02)
α-Phenylthio substituted amines have been found to be convenient reagents for the preparation of the pyrrolidine ring.Benzylamine (2) undergoes 1,3-dipolar cycloaddition with several dipolarophiles in the presence of silver fluoride.The reaction is believed to proceed via the intermediacy of an azomethine ylide.Treatment of α-(phenylthio)cyanoamines 10 and 17 with strong base results in the loss of the phenylthio group, and formation of substituted trans-piperazines 21, 22 in the case of 17.The mechanism of the reaction involves dimerization of the initially formed cyano substituted azomethine ylide intermediate, which behaves as a captodative diradical.Finally, the reaction of several alkenylamines with tributyltin hydride was studied as a method for generating the pyrrolidine ring via a radical cyclization reaction.