Diethyl Trichloromethylphosphonate Research Articles

A DFT study of the mechanism and regioselectivity of the reaction between diethyl trichloro-methyl phosphonate and diphenyl methyl phosphinite

The reaction of diethyl trichloro-methyl phosphonate (C1) with diphenyl methyl phosphinite (C2), has been scrutinized within the Density Function Theory at the B3LYP/6-311(d,p) computational level. The regiosomeric reaction paths involving the two center of compound (C1) have been studied. DFT calculations account for the high regioselectivity in the chlorine atom, in complete agreement with the experimental outcomes.

One-pot stereoselective synthesis of (Z)-diethyl α-chlorovinylphosphonates

Diethyl trichloromethylphosphonate, treated with BuLi followed by an aldehyde (or cycloalkenone), was converted to α-chlorovinylphosphonates via the intermediate formation of a bisphosphonate and a Wadsworth–Emmons olefination. High (Z) stereoselectivity of the reaction is discussed in terms of the conformational preferences of the adducts.

ChemInform Abstract: New Route to 1‐Formylalkylphosphonates Using Diethyl Trichloromethylphosphonate as a Precursor.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Lithiation of diethyl trichloromethylphosphonate and the transformations of the α-lithiated derivative

The lithiation of diethyl trichloromethylphosphonate below –100 °C leads to a stable α-lithiated derivative, but at temperatures of about –80 °C the lithiation is accompanied by spontaneous reactions leading to tetraethyl (chloromethylene)bisphosphonate as the exclusive product. Possible mechanisms of the reaction are discussed.

New route to 1-formylalkylphosphonates using diethyl trichloromethylphosphonate as a precursor

Diethyl trichloromethylphosphonate 1 and chlorotrimethylsilane were converted in a three-step sequence by BuLi into α-phosphorylated α-silylated α-substituted carbanions 4. These, on reaction with ethyl formate in the presence of chlorotrimethylsilane give transient silylated acetals 8 which readily undergo acid hydrolysis to afford 1-formylalkylphosphonates 7 in good yield.

ChemInform Abstract: Addition of Diethyl Trichloromethylphosphonate to Olefins Catalyzed by Copper Complexes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Addition of diethyl trichloromethylphosphonate to olefins catalysed by copper complexes

Diethyl trichloromethyl phosphonate is added on olefins by non-chain catalytic reactions catalysed by copper amine complexes.

A high yield route to ethyl esters of car☐ylic acids

Diethyl trichloromethylphosphonate reacts with car☐ylic acids to yield their ethyl esters, via transesterification; even the hindered mesitoic acid is esterified in high yield.

Reactions of diethyl trichloromethylphosphonate with metallic zinc

Complexes of tetrachloroethylenediphosphonic acid tetraethyl ester and diethyl trichloromethylphosphonate (DETCMP) with ZnCl 2 are shown to be formed in the reaction of DETCMP with metallic zinc. The complexes undergo dealkylation and condensation reactions leading to the formation of zinc polypyrophosphonate: ▪. Alcoholic solvents cause an increase of reaction rate.

Halomethyl—metal compounds : LXIII. Diethyl lithiodichloromethylphosphonate and tetraethyl lithiochloromethylenediphosphonate

The action of n-butyllithium in THF at low temperature on diethyl trichloromethylphosphonate and tetraethyl dichloromethylenediphosphonate gave the reagents LiCCl 2P (O) (OEt) 2 and [(EtO) 2(O)P] 2CClLi, respectively. The hydrolyses of these reagents, some coupling reactions with dimethyl sulfate, allyl bromide and trimethylchlorosilane and their use in the synthesis of chloroolefins are described.

Fluoride-induced cleavage of the carbon-phosphorus bond in diethyl trichloromethylphosphonate. Source of dichlorocarbene and dialkyl phosphorofluoridates

Fluoride-induced cleavage of the carbon-phosphorus bond in diethyl trichloromethylphosphonate. Source of dichlorocarbene and dialkyl phosphorofluoridates

The reactivity of organophosphorus compounds. Part XXII. Preparation of diethyl trichloromethylphosphonite and diethyl dichloromethylphosphonate

Diethyl trichloromethylphosphonite has been prepared from trichloromethyldichlorophosphine and ethanol in the presence of base, and some of its reactions have been investigated. Diethyl dichloromethylphosphonate has been obtained by reaction of triethyl phosphite with diethyl trichloromethylphosphonate in hexanol.