100879-87-6Relevant academic research and scientific papers
Enantioselective acylphosphonylation-dual lewis acid-lewis base activation of aldehyde and acylphosphonate
Wen, Ye-Qian,Hertzberg, Robin,Moberg, Christina
, p. 6172 - 6178 (2014)
Acetoxyphosphonates were obtained by a one-step procedure consisting of reaction of diethyl acetylphosphonate with prochiral aldehydes in the presence of a catalytic system comprising a chiral Lewis acid, an achiral Lewis base, and a Br?nstedt base. Best
Facile and high-yielding preparation of α-acetoxyphosphonates from α-hydroxyphosphonates assisted by microwave irradiation
Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara,Amoozgar, Zohreh
, p. 1771 - 1774 (2004)
A convenient and eco-friendly procedure is described for the efficient preparation of a variety of α-acetyloxyphosphonates from their corresponding α-hydroxyphosphonates using acetic anhydride under microwave irradiation in the absence of solvent.
Iron-doped single-walled carbon nanotubes as new heterogeneous and highly efficient catalyst for acylation of alcohols, phenols, carboxylic acids and amines under solvent-free conditions
Sharghi, Hashem,Jokar, Mahboubeh,Doroodmand, Mohammad Mahdi
experimental part, p. 426 - 442 (2011/04/15)
Iron-doped single-walled carbon nanotubes (Fe/SWCNTs) represent an efficient and new heterogeneous reusable catalyst for the acylation of a variety of alcohols, phenols, carboxylic acids and amines with acid chlorides or acid anhydrides under solvent-free conditions. The reactions of various primary, secondary, tertiary, and benzylic alcohols, diols, phenols, as well as aromatic and aliphatic amines give acylated adducts in good to excellent yields.
Copper Triflate as a Useful Catalyst for the High-Yielding Preparation of α-Acetyloxyphosphonates under Solvent-Free Conditions
Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara,Amoozgar, Zohreh
, p. 295 - 297 (2007/10/03)
A high-yielding and convenient procedure for the efficient conversion of α-hydroxyphosphonates to α-acetyloxyphosphonates using acetic anhydride in the presence of catalytic amounts of copper triflate is described.
The Nature of Cationic Intermediates Derived from α-Thiophosphoryl and α-Thiocarbonyl Mesylates. Neighboring Thiophosphoryl and Thiocarbonyl Participation
Creary, Xavier,Mehrsheikh-Mohammadi, M. E.
, p. 7 - 15 (2007/10/02)
A series of mesylate derivatives of α-hydroxy thiophosphonathes, RCH(OMs)PS(OEt)2 (8), have been prepared.These mesylates can react by kc processes under solvolytic conditions if cation stabilizing groups such as p-anisyl or p-thioanisyl groups are present.However, under conditions of appropriate electron demand, mesylates 8 can react by kΔ processes involving thiophosphoryl participation.The cyclic intermediate ions capture acetic acid at phosphorus and lead ultimately to α-thio acetate derivatives of phosphonates.This overall transformation converts the P=S function to the P=O group.Rates of acetolyses of 8 can exceed those of the O-phosphoryl analogues by large factors when kΔ processes are involved (as expected for anchimerically assisted processes).Mesylate derivatives of α-hydroxy thio esters, R2C(OMs)CSOCH3 (9), can also react by kΔ processes as shown by enhanced rates relative to simple ester analogues.The substrate (R)-(-)-PhCH(OMs)CSOCH3 (38) gives an acetolysis product that is largely retained, while 9 (R = Me) gave a large fraction of a rearranged product.These data all argue in favor of neighboring thiocarbonyl participation in 8, giving cyclized intermediate cations.The behavior of mesylates 8 and 9 can therefore be quite different from that of the corresponding O-phosphoryl and carbonyl analogues.Neighboring group participation in 8 and 9 accounts for the differences.The contrasting behavior of 8 and 9 also argues against neighboring phosphoryl or carbonyl participation in solvolyses of mesylate derivatives of α-hydroxy phosphonates or α-keto mesylates.
