67815-92-3Relevant articles and documents
Deamination Reactions, 41. Reactions of Aliphatic Diazonium Ions and Carbocations with Ethers
Kirmse, Wolfgang,Jansen, Ulrich
, p. 2607 - 2625 (2007/10/02)
Aliphatic diazonium ions and carbocations were generated by deacylation of appropriate nitrosoureas (1, 5, 9) in alcohol-ether mixtures or in 2-alkoxyethanols.Ethers were generally inferior to alcohols in capturing cationic intermediates.Formation of trialkyloxonium ions led to alkyl exchange or ring opening.The observed reactivity orders were n-butyl > isobutyl for the diazonium ions, allyl > sec-butyl > tert-butyl for the carbocations, methoxy > ethoxy and oxirane > oxetane > tetrahydrofuran for the ethers, indicating the predominance of steric effects.Neighboring group participation in 4-methoxy-1-butanediazonium ions (58) and 4,5-epoxy-1-pentanediazonium ions (74) was detectable but inefficient ( 20percent of cyclic oxonium ions).