2594-06-1Relevant articles and documents
P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids
Meng, Haiwen,Sun, Kunhui,Xu, Zhimin,Tian, Lifang,Wang, Yahui
supporting information, p. 1768 - 1772 (2021/03/26)
An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.
Revisiting Arene C(sp2)?H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway
Hwang, Yeongyu,Park, Yoonsu,Kim, Yeong Bum,Kim, Dongwook,Chang, Sukbok
supporting information, p. 13565 - 13569 (2018/09/25)
Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C?H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed.
Direct Conversion of Hydroxamic Acids into Nitriles
Liguori, Angelo,Sindona, Giovanni,Romeo, Giovanni,Uccella, Nicola
, p. 168 (2007/10/02)
Aromatic and aliphatic nitriles are prepared in excellent yield from the corresponding hydroxamic acids and phosphorus tribromide in benzene solution.