1529-78-8Relevant articles and documents
Synthesis of olefins via a Wittig reaction mediated by triphenylarsine
Li, Lun,Stimac, Jared C.,Geary, Laina M.
supporting information, p. 1379 - 1381 (2017/03/17)
An arsine-mediated Wittig reaction for the synthesis of olefins is described. After heating triphenylarsine in the presence of an activated alkyl bromide for 30?min, the resulting arsonium salt condensed with aldehydes in as little as 5?min at room temperature, yielding the olefins in high yields. Aromatic, heteroaromatic, and alkyl aldehydes were all suitable substrates for this process.
The reaction of partially protected aldoses with stabilized arsonium ylides: Synthesis of E acyclic unsaturated derivatives and C-glycosyl derivatives
Lievre, Catherine,Frechou, Catherine,Demailly, Gilles
, p. 1 - 15 (2007/10/03)
The reaction of partially protected aldoses with (carbomethoxymethyl)triphenylarsonium bromide and zinc in toluene gave E α,β-unsaturated acyclic esters. When intramolecular transesterification occurred, bicyclic 1,4-lactone derivatives were formed concurrently. Otherwise, using these non alcaline conditions, olefination did not favour the formation of C-glycosyl derivatives. On the other hand, when the reaction was performed with (carbomethoxymethylene)triphenylarsorane in toluene, followed by the addition of n-butyllithium, bicyclic derivatives were obtained rapidly in good yields. Moreover, when cyanomethyltriphenylarsonium bromide was used in place of (carbomethoxymethyl)triphenylarsonium bromide, the corresponding E aldooctenonitriles were produced in satisfactory yields.
