1362101-12-9Relevant academic research and scientific papers
Synthesis of five-membered unsaturated compounds from ketones via cyanophosphates under neutral conditions: [1,5]-C–H insertion of alkylidene carbenes generated by tetrazole fragmentation
Yoneyama, Hiroki,Uemura, Kenji,Usami, Yoshihide,Harusawa, Shinya
, p. 6109 - 6117 (2017/09/29)
Cyanophosphates (CPs) can easily be prepared via the reactions of carbonyl compounds with diethyl phosphorocyanidate (DEPC) in the presence of LiCN (cat.) under non-aqueous conditions. Treatment of ketone-derived CPs with TMSN3/Bu2Sn
Dehydrative fragmentation of 5-hydroxyalkyl-1 h -tetrazoles: A mild route to alkylidenecarbenes
Wardrop, Duncan J.,Komenda, John P.
supporting information; experimental part, p. 1548 - 1551 (2012/06/05)
The development of a mild, base-free method for the generation of alkylidenecarbenes is reported. Treatment of 5-hydroxyalkyl-1H-tetrazoles with carbodiimides generates products arising from the 1,2-rearrangement or [1,5]-C-H bond insertion of a putative alkylidenecarbene. Formation of this divalent intermediate is proposed to occur by way of a tetraazafulvene, which undergoes extrusion of 2 mol of dinitrogen. Details of this methodology, its application to the synthesis of combretastatin A-4, and an improved route to 5-hydroxyalkyl-1H-tetrazoles are described.
