52113-82-3Relevant academic research and scientific papers
Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy
Shaw, Megan H.,Croft, Rosemary A.,Whittingham, William G.,Bower, John F.
, p. 8054 - 8057 (2015)
A short entry to substituted azocanes by a Rh-catalyzed cycloaddition-fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible.
Reactions of Cyclopropyl Sulfonates with Nucleophiles: SN2 Displacements at Cyclopropanes with Inversion
Banert, Klaus
, p. 1564 - 1574 (2007/10/02)
Treatment of cyclopropyl trifluoromethanesulfonate (3) with tributylhexadecylphosphonium azide (QN3) in aprotic solvents almost quantitatively afforded cyclopropyl azide (6) in a second-order reaction.Nucleophilic displacements with ring preservation were also achieved using QCN or QBr.The analogous reactions of the epimeric 2-methylcyclopropyl trifluoromethanesulfonates (16, 17) with QN3 highly stereospecifically yielded the 2-methylcyclopropyl azides (24, 25) with inversion in addition to the allylic azides 27, 28, and 29.The product fraction of cyclic azides decrea sed with growing steric hindrance in the order 3 > 16 > 17.The experimental results show that SN2 displacements take place with clean inversion at the cyclopropane carbon atom.
