97663-40-6Relevant articles and documents
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.
PALLADIUM CATALYZED SYNTHESIS OF ALLYLIC SULFONES. UTILIZATION OF α-NITRO OLEFINS AS ALLYLIC NITRO COMPOUNDS
Tamura, Rui,Hayashi, Koji,Kakihana, Masato,Tsuji, Masanori,Oda, Daihei
, p. 229 - 232 (2007/10/02)
α-Nitro olefins reacted with sodium benzenesulfinate in the presence of tertiary amine and palladium(0) catalyst to afford allylic sulfones.The competition experiment showed that relative rate of the sulfonylation of an α-nitro olefin to that of the corre
