922-29-2Relevant articles and documents
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.