104507-97-3Relevant academic research and scientific papers
A PRACTICAL ACCESS TO ALLYLIC SULPHONES AND LACTONES FROM ALLYLIC NITRO COMPOUNDS
Barlaam, Bernard,Boivin, Jean,Zard, Samir Z.
, p. 7429 - 7432 (2007/10/02)
Allylic nitro derivatives can be readily solvolysed in aqueous acetic acid to give allylic sulphones in the presence of a sulphinate salt or allylic lactones if the substrate contains a suitably located ester group.
Palladium-Catalyzed Substitutions of Allylic Nitro Compounds. Regiochemistry
Tamura, Rui,Kai, Yoshiki,Kakihana, Masato,Hayashi, Koji,Tsuji, Masanori,et al.
, p. 4375 - 4385 (2007/10/02)
Primary, secondary, and tertiary allylic nitro compounds underwent Pd(0)-catalyzed allylic substitution by stabilized carboanions, secondary amines, and benzenesulfinate ion (PhSO2-). α,β-disubstituted α-nitro olefins also behaved as allylic nitro compounds, via base-catalyzed vinyl -> allyl rearrangement, and underwent allylic substitution by secondary amines and PhSO2-.The regiochemistry of these substitutions was dependent on the structure of the allylic nitro compound amd on the steric bulk of the nucleophile.Generally, substitution occurred at the lesshindered or least substituted site.In some cases added or generated NaNO2 affected the regioselectivity of the allylic substitution of allylic nitro compounds and some allylic acetates by PhSO2-.Under these conditions, the more sterically hindered allylic sulfones were formed.
