1520095-40-2Relevant articles and documents
Reaction of [HO(CH 2) 3] 3P with ,β -unsaturated ketones containing a phenylpropanoid backbone
Moiseev,James,Gushchin
, p. 242 - 254 (2014/01/06)
Interaction of 3,4-(MeO)2-benzylideneacetone with [HO(CH2)3]3P (THPP) was studied in CD3OD by NMR to compare reactivity of a phenylpropanoid ,β-unsaturated ketone with a corresponding ,β-unsaturated aldehyde. In the presence of HCl, both the ketone and a related cinnamaldehyde first establish an equilibrium with the product formed by nucleophilic attack of the THPP at the CO bond, [ArCHCHCX(OD)PR3]+Cl-(XH or CH3, ArPh or 3,4-(MeO)2C6H3). The ketone salt then slowly transforms into [R3PCH(Ar)CH(D)C(O)CD3]+Cl-, the phosphonium product of nucleophilic attack of THPP at the CC bond, whereas the final product from the aldehyde is the (-ether)phosphonium chloride [ArCHCHCH(OCD3)PR3] +Cl-. In aqueous media, in the absence of HCl, 4-HO-benzylideneacetone, which is similar to a lignin-type, ,β-unsaturated aldehyde model compound, interacts with THPP to afford a stable phosphonium zwitterion, in contrast to the previously studied aldehyde model, which forms dimeric, bisphosphonium products.