1080-41-7Relevant academic research and scientific papers
Silver-Catalyzed Oxidative C(sp3)?P Bond Formation through C?C and P?H Bond Cleavage
Li, Lili,Huang, Wenbin,Chen, Lijin,Dong, Jiaxing,Ma, Xuebing,Peng, Yungui
supporting information, p. 10539 - 10544 (2017/08/22)
The silver-catalyzed oxidative C(sp3)?H/P?H cross-coupling of 1,3-dicarbonyl compounds with H-phosphonates, followed by a chemo- and regioselective C(sp3)?C(CO) bond-cleavage step, provided heavily functionalized β-ketophosphonates. This novel method based on a readily available reaction system exhibits wide scope, high functional-group tolerance, and exclusive selectivity.
[2 + 2] cycloaddition of cyclic vinyl phosphonates with ketenes
Ruder, Suzanne M.,Ding, Min
, p. 1771 - 1776 (2007/10/03)
Highly substituted cyclic β-alkoxyvinyl phosphonates underwent thermal [2+2] cycloaddition with activated ketenes to afford bicyclic phosphonates. Fragmentation of the central polarized bond of this bicyclic system occurred readily upon treatment with zin
A New Synthesis of Cyclic β-Keto Phosphonates from α-Nitro Epoxides and a Dialkyl Phosphite
Kim, Dae Young,Kong, Myeon
, p. 3359 - 3360 (2007/10/02)
Cyclic β-keto phosphonates are readily prepared in good yields by the reaction of a dialkyl phosphite anion and α-nitro epoxides.
Reaction of Diethyl Phosphorochloridite with Enolates: A General Method for Synthesis of β-Keto Phosphonates and α-Phosphono Esters through C-P Bond Formation
Lee, Koo,Wiemer, David F.
, p. 5556 - 5560 (2007/10/02)
The reaction of ketone enolates with diethyl phosphorochloridite, followed by air oxidation of the intermediate reaction products, has proven to be a general and convenient method for preparation of β-keto phosphonates.Fourteen β-keto phosphonates have been prepared by this method, in an average yield greater than 60percent.This procedure also appears to be applicable to preparation of both α-phosphono aldehydes and α-phosphono esters.Although special precautions may be necessary to avoid aldol condensation during formation of aldehyde enolates, in two cases it was shown that the resulting enolates react readily with diethyl chlorophosphite.Finally, a set of five ethyl esters was converted to α-phosphono esters by this method.Yields of the α-phosphono esters are influenced by steric hindrance at the enolate carbon, but the average yield for this series was ca. 70percent.Because this synthetic method relies upon an electrophilic phosphorus reagent for formation of the C-P bond, it is complementary to the traditional Arbuzov synthesis.On the basis of the 21 examples presented here, it appears to be more widely applicable.
PHOSPHORYLATION OF 1-MORPHOLINOCYCLOHEXENE AND CYCLOPENTENE. CONVENIENT METHOD OF SYNTHESIS OF α-PHOSPHORYLATED DERIVATIVES OF CYCLOHEXANONE AND CYCLOPENTANONE
Tolmachev, A. A.,Kostyuk, A. N.,Morozova, L. N.,Lampeka, R. D.,Kozlov, E. S.,Pinchuk, A. M.
, p. 1475 - 1484 (2007/10/02)
It was shown that 1-morpholinocyclopentene and 1-morpholinocyclohexene are readily phosphorylated by phosphorus(III) halides in the presence of triethylamine.From the compounds obtained, α-phosphorylated cyclopentanones and cyclohexanones were synthesized
Synthesis of β-Keto Phosphonates from Vinyl Phosphates via a 1,3-Phosphorus Migration
Calogeropoulou, Theodora,Hammond, Gerald B.,Wiemer, David F.
, p. 4185 - 4190 (2007/10/02)
A new method for the preparation of β-keto phosphonates has been developed, involving rearrangement of vinyl phosphates upon treatment with strong base.Because this approach ultimately relies upon electrophilic dialkyl phosphorochloridates as the phosphor
THE 1,3-MIGRATION OF PHOSPHORUS FROM OXYGEN TO CARBON: A NEW SYNTHESIS OF β-KETOPHOSPHONATES FROM ENOL PHOSPHATES
Hammond, Gerald B.,Calogeropoulou, Theodora,Wiemer, David F.
, p. 4265 - 4268 (2007/10/02)
Enol phosphates, readily prepared from ketone enolates and dialkyl phosphorochloridate, can be converted to the analogous β-ketophosphonates by treatment with straong base.
Reaction of 2-Chlorooxiranes with Phosphites and Phosphanes: A New Route to β-Carbonylphosphonic Esters and -phosphonium Salts
Herzig, Christian,Gasteiger, Johann
, p. 601 - 614 (2007/10/02)
Reaction of alkylsubstituted 2-chlorooxiranes 6 with trialkyl phosphites 11 gives β-carbonylphosphonic diesters (12a, b, 15a, b, 20a, 21a), free of isomeric enol phosphates or α,β-epoxyphosphonates. 2-Chloro-2-(chloromethyl)oxirane (6c) undergoes with 11 an Arbusov reaction followed by a Perkow reaction ( -> 18 -> 17).The limitation of the method is probed with sterically crowded substituents in 3-position of 6. 6b yields with triphenylphosphane a β-ketophosphonium salt (23), which can be converted to a keto-ylide (24).
β-Ketophosphonsaeureester aus α-chloroxiranen
Gasteiger, Johann,Herzig, Christian
, p. 2687 - 2688 (2007/10/02)
β-Ketophosphonic ester can be obtained by the treatment of α-chloroepoxides with trialkylphosphites.
