64255-45-4Relevant academic research and scientific papers
Reactivity of aldehydes with semi-stabilised arsonium ylide anions: Synthesis of terminal (E)-l,3-dienes
Habrant, Damien,Stengel, Bruno,Meunier, Stephane,Mioskowski, Charles
, p. 5433 - 5440 (2008/02/10)
A study of the reactivity of semi-stabilised arsonium ylide anions in olefinalion reactions is presented. The different ylide anions were generated by the addition of nBuLi to various arsonium halide derivatives: [Ph 2As(R)R']+X , where R and R′ are methyl, allyl, prenyl or benzyl groups. By using diallyldiphenylarsonium bromide (R = R′ = allyl) an olefinationprotocol was optimised allowing the efficient transformation of aliphatic aldehydes into terminal 1,3-dienes with a high selectivity for the E isomer (E/Z ratios ranging from 90:10 to 97:3). The olefination reactions of aldehydes with dissymmetric arsonium halides (R≠R′) are very chemoselective; with arsonium ylide anions the benzyl moiety is more reactive than the allyl moiety which is much more reactive than prenyl and methyl groups. Based on the experimental results, a mechanism is proposed for the reaction.
Regio- and Stereoselective Hydrosulfonylation of Conjugated Dienes via a (?-Allyl)palladium Complex
Tamaru, Yoshinao,Yamada, Yoshimi,Kagotani, Masahiro,Ochiai, Hirofumi,Nakajo, Eiji,et al.
, p. 4669 - 4681 (2007/10/02)
The combination of a sulfonylpalladation of acyclic dienes 1 (with 2 equiv of NaSO2R and 1 equiv of PdCl2 in acetic acid or acetic acid-H2O at 50-80 deg C under air) and a protiodepalladation of the thus obtained palladium complexes 3 with dimethylglyoxime (in a protic solvent at room temperature) provides di- and trisubstituted (Z)-Δ3-sulfones 12 selectively, irrespective of the stereochemistry of the starting dienes.Similar treatment of 1-vinylcycloalkenes 5 (n (1,3) strain between Pd and the substituent on the allylic position.
