60622-52-8Relevant academic research and scientific papers
Reaction of allylic and benzylic alcohols and esters with PPh 3/I2: One-pot synthesis of β,γ-unsaturated compounds
Alvarez-Manzaneda,Chahboun,Cabrera Torres,Alvarez,Alvarez-Manzaneda,Haidour,Ramos López
, p. 3755 - 3759 (2005)
The treatment of tertiary and secondary allylic alcohols containing a terminal double bond, and their acetyl derivatives, with triphenylphosphine and iodine under mild conditions leads regiospecifically and in high stereoselectivity to the corresponding primary allylic iodides, which can react 'in situ' with diverse nucleophiles. Primary allylic alcohols and benzyl alcohols and acetates are also transformed into the corresponding iodides under these conditions.
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.
Regioselective Preparation of Allylic Sulfones by Palladium-Catalyzed Reactions of Allylic Nitro Compounds with Sodium Benzenesulfinate
Ono, Noboru,Hamamoto, Isami,Kawai, Takashi,Kaji, Aritsune,Tamura, Rui,Kakihana, Masato
, p. 405 - 410 (2007/10/02)
Treatment of allylic nitro compounds with sodium benzenesulfinate in the presence of 5 molpercent of Pd(PPh3)4 in N,N-dimethylformamide (DMF) at 20-70 deg C for 1-10 h resulted in the formation of allylic sulfones with predominance of kinetically controll
Carbon Dioxide-Promoted Telomerization of 1,2- and 1,3-Dienes with Benzenesulfinate Catalyzed by Palladium(0)
Inoue, Yoshio,Hashimoto, Harukichi
, p. 3705 - 3708 (2007/10/02)
The telomerization of 1,2- and 1,3-dienes with benzenesulfinate dihydrate catalyzed by palladium(0) has been promoted by the presence of carbon dioxide
REGIOSELECTIVE SYNTHESIS OF ALLYLIC SULFONES BY PALLADIUM-CATALYZED DENITRO-SULFONYLATION OF ALLYLIC NITRO COMPOUNDS
Tamura, Rui,Hayashi, Koji,Kakihana, Masato,Tsuji, Masanori,Oda, Daihei
, p. 851 - 854 (2007/10/02)
Allylic nitro compounds undergo denitro-sulfonylation catalyzed by Pd(PPh3)4 or Pd(PPh3)4+NaNO2 with PhSO2Na*2H2O to afford allylic sulfones regioselectively.
NUCLEOPHILIC SUBSTITUTION REACTIONS OF ALLYLIC ESTERS CATALYSED BY PALLADIUM-GRAPHITE AND RELATED HETEROGENEOUS CATALYSTS
Boldrini, Gian Paolo,Savoia, Diego,Tagliavini, Emilio,Trombini, Claudio,Umani-Ronchi, Achille
, p. 97 - 106 (2007/10/02)
Highly dispersed palladium on graphite (Pd/Gr), carbon (Pd/C) and alumina (Pd/Al2O3) have been employed as catalysts in substitution reactions of allylic esters with nucleophiles such as benzenesulfinate and diethyl malonate anions, and 1-(1-cyclohexen-1-yl)pyrrolidine.
