84602-97-1Relevant academic research and scientific papers
Phase transfer catalysis (ptc): a convenient tool for generation and reactions of allyl sulphonyl carbanions
Jonczyk, Andrzej,Radwan-Pytlewski, Tadeusz
, p. 111 - 119 (2007/10/03)
Allyl sulphones la-d or le react with alkyl halides (RX) in the presence of concentrated aqueous NaOH solution and tetrabutylammonium bromide (TBAB) as a catalyst to give, with high yields, mono(2a-d) or di-alkylated (3e) products, respectively. Under the same conditions sulphone If forms mixtures of the products, the composition of which depends on the structure of RX and the RX:lf ratio. With a,cu-dibromo alkanes, sulphones la,d-f give rise to cyclic products (7a,d-f) with low to excellent yields. With 4-nitrofluorobenzene (in solid NaOH-DMSO system) or vinyl acetate (by PTC) sulphone la affords the products 2al3 and 9a, respectively.
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.
Application of the Catalytic Two-Phase System to Carbanionic Reactions of Allyl Sulfones
Jonczyk, Andrzej,Radwan-Pytlewski, Tadeusz
, p. 910 - 912 (2007/10/02)
Allyl sulfones are easily converted into carbanions in the presence of concentrated aqueous NaOH solution and a quaternary ammonium catalyst.These carbanions readily react with alkyl halides, electrophilic alkenes, or perchloroalkanes.
