96258-65-0Relevant academic research and scientific papers
A convenient and mild protocol for preparation of α – trimethylsilyloxyphosphonates using sulfamic acid and their oxidation to α – ketophosphonates in the presence of N-bromosuccinimide
Mitragotri, Satish D.,Kulkarni, Makarand A.,Desai, Uday V.,Wadagaonkar, Prakash P.
, (2021/10/05)
A convenient and mild protocol was developed for the trimethylsilylation of α-hydroxyphosphonates using hexamethyldisilazane as the silylating agent in the presence of sulfamic acid (SA) as a heterogeneous solid acid catalyst in dichloromethane as the rea
Iron(III) trifluoroacetate [Fe(F3CCO2)3] as an easily available, non-hygroscopic, non-corrosive, highly stable and a reusable Lewis Acid catalyst: Efficient O-silylation of α-hydroxyphosphonates, alcohols and phenols by he
Firouzabadi, Habib,Iranpoor, Nasser,Jafari, Abbas Ali,Jafari, Mohammad Reza
, p. 2711 - 2714 (2008/12/20)
O-Silylation of hydroxyl groups of α-hydroxyphosphonates, primary, secondary tertiary-alcohols and phenols with HMDS was achieved in high to excellent yields using iron(III) trifluoroacetate [Fe(F3CCO2)3] as an easily avai
Aluminium triflate [Al(OTf)3] as a recyclable catalyst for the conversion of α-hydroxyphosphonates, alcohols and phenols to their corresponding O-silylated products with hexamethyldisilazane (HMDS)
Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara,Ghassamipour, Soheila
, p. 595 - 599 (2007/10/03)
Al(OTf)3 as a recyclable catalyst conducts the efficient conversion of various types of α-hydroxyphosphonates to their corresponding α-trimethysilyloxyphosphonates with HMDS in the absence of solvent at room temperature. The general applicabili
Magnesium triflate [Mg(OTf)2] a highly stable, non-hygroscopic and a recyclable catalyst for the high yielding preparation of diethyl α-trimethylsilyloxyphosphonates from diethyl α-hydroxyphosphonates by HMDS under solventless conditions
Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara,Ghassamipour, Soheila
, p. 3197 - 3202 (2007/10/03)
A broad, adaptable, high yielding and convenient procedure for the easy conversion of various α-hydroxyphosphonates to α-trimethylsilyloxyphosphonates under mild conditions with HMDS in the presence of a catalytic amount of magnesium triflate as a highly stable and a non-hygroscopic recyclable catalyst in neat conditions is described. In order to show the general applicability of this method, we have also applied this procedure successfully for the silylation of ordinary alcohols and phenols.
Copper triflate [Cu(OTf)2] is an efficient and mild catalyst for the silylation of α-hydroxyphosphonates to α-trimethylsilyloxyphosphonates with HMDS at room temperature
Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara,Ghassamipour, Soheila,Amoozgar, Zohreh
, p. 891 - 893 (2007/10/03)
A broad, adaptable, high yielding and convenient procedure for the fast conversion of various α-hydroxyphosphonates to α-trimethylsilyloxyphosphonates under mild conditions with HMDS in the presence of a catalytic amount of copper triflate is described. T
A high yielding preparation of α-trimethylsilyloxyphosphonates by silylation of α-hydroxyphosphonates with HMDS catalyzed by iodine
Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara
, p. 3653 - 3655 (2007/10/03)
A general, versatile, high yielding and convenient procedure for the immediate conversion of various α-hydroxyphosphonates to α-trimethylsilyloxyphosphonates under neutral conditions using HMDS in the presence of a catalytic amount of iodine is described.
Stabilization Demands of Diethyl Phosphonate Substituted Carbocations as Revealed by Substituent Effects
Creary, Xavier,Underiner, Ted L.
, p. 2165 - 2170 (2007/10/02)
Trifluoroethanolyses of a series of mesylate derivatives of diethyl (1-aryl-1-hydroxymethyl)phosphonates, 9, gave a Hammett ρ value of -10.1 in the electron donor substituent region.This value was slightly less than the value of -11.6 seen in the corresponding benzyl mesylates, ArCH2OMs, 12, in hexafluoroisopropyl alcohol.These data suggest that the demand for aryl group stabilization in the intermediate phosphoryl-substituted cation 10 does not surpass that of the α-H analogues, the benzyl cations.Some other factor must therefore account for the relative ease of formation of cations 10, which have the electronegative diethyl phosphonate group attached directly to the cationic center.The likely factor is an offsetting cation stabilizing feature associated with the diethyl phosphonate group.The Hammett plots for both mesylates 9 and 12 show a break, with decreased ρ values (-6.1 and -5.1, respectively) being observed in the electron-withdrawing region of the plot.Solvent effect studies on 9-m-F suggested that a change to "borderline behavior" is the origin of the break in the Hammett plot.A mechanistic change to the kδ process could be ruled out.The triflate derivative of diethyl (1-hydroxyethyl)phosphonate, 14, gave mixtures of substitution and elimination products on solvolysis.Solvent effect studies indicated a largely nucleophilic mechanism, while isotope effect studies were in line with some cationic character in the transition state in the highly ionizing, nonnucleophilic hexafluoroisopropyl alcohol solvent.Ion pair formation or the SN2 (intermediate) mechanism could rationalize the behavior of 14 in more highly ionizing solvents.
