29509-37-3Relevant articles and documents
Cyclopentanone as a cation-stabilizing electron-pair donor in the calcium-catalyzed intermolecular carbohydroxylation of alkynes
Stopka, Tobias,Niggemann, Meike
supporting information, p. 1437 - 1440 (2015/03/30)
Although they have been used as reactivity-controlling additives in cationic polymerizations for decades, Lewis basic electron pair donor (ED) compounds were never used for the stabilization of cationic intermediates in transformations of small molecules. As such an ED, cyclopentanone proved highly efficient for the stabilization of allyl and vinyl cations in combination with our calcium-based catalyst system. Therefore, the first general transition-metal-free intermolecular carbohydroxylation of alkynes with allyl and propargyl alcohols was realized.
Transition from π radicals to σ radicals: Substituent-tuned cyclization of hydrazonyl radicals
Duan, Xiao-Yong,Zhou, Neng-Neng,Fang, Ran,Yang, Xiu-Long,Yu, Wei,Han, Bing
, p. 3158 - 3162 (2014/04/03)
Hydrazonyl radicals are known for their π-electronic structures; however, their σ-electronic structures have not been reported as yet. Herein, we show that readily accessible β,γ- and γ,δ- unsaturated N-trichloroacetyl and N-trifluoroacetyl hydrazones can be conveniently converted into hydrazonyl σ radicals, which subsequently undergo 5-exo-trig radical cyclization at the N1 or N2 atom to form pyrazolines and azomethine imines, respectively. Time for a radical career change? Known for their π character, hydrazonyl radicals can be tuned to act as σ radicals with the spin density delocalized on both nitrogen atoms by attaching a trifluoroacetyl or trichloroacetyl group to the N 1 atom. The hydrazonyl σ radicals derived from the corresponding N-acyl-substituted β,γ- and γ,δ-unsaturated hydrazones underwent Ci-N1 and Ci-N2 bond-forming 5-exo-trig cyclization, respectively (see scheme).
Highly efficient Narasaka-Heck cyclizations mediated by P(3,5-(CF 3)2C6H3)3: Facile access to N-heterobicyclic scaffolds
Faulkner, Adele,Bower, John F.
, p. 1675 - 1679 (2012/04/05)
N-heterobicyclic scaffolds: Highly efficient palladium-catalyzed cyclizations of oxime esters with cyclic alkenes were used as a general entry to perhydroindole and related scaffolds. The chemistry is reliant upon the use of P(3,5-(CF3)2/