58580-13-5Relevant academic research and scientific papers
β-Bromoenol phosphate as a new precursor for the modular regioselective synthesis of substituted furans
Fernandes, Rushil,Mhaske, Krishna,Narayan, Rishikesh
supporting information, (2021/11/24)
Owing to its importance in various realms of chemistry, furan occupies a position of eminence among heterocycles. Despite the availability of many methodologies for the synthesis of variably substituted furans, a modular convenient synthesis of 2,4-disubstituted furans remains challenging. The present work attempts to bridge that gap through a novel annulation-based approach using feedstock chemicals such as methyl ketones and their easily available derivatives, β-bromoenol phosphates. We have demonstrated a hitherto unknown reactivity of β-bromoenol phosphates which is responsible for the observed regioselectivity. The reaction requires only sodium hydride as the base under mild conditions. The scope of the reaction was found to be broad with the possibility of obtaining even tri-substituted furans besides a variety of 2,4-disubstituted furans. The methodology was applied to obtain synthetically challenging 3-acylfuran derivatives as well. The newly developed methodology is characterized by the modularity, regioselectivity as well as its practicality owing to easily available starting materials and fast reaction times.
A simple and efficient synthesis of [2H10]deuterated bromfenvinphos by the Perkow reaction
Huras, Bogumiaa,Konopski, Leszek,Zakrzewski, Jerzy
scheme or table, p. 399 - 400 (2012/06/04)
(E,Z)-2-bromo-1-(2,4-dichlorophenyl)vinyl bis[ethyl-2H 5] phosphate ([2H10]bromfenvinphos), a regiospecifically deuterium-labelled pesticide, was synthesized in two steps starting from [2H6]ethanol, phosphorus trichloride and 2,4-dichlorophenacylidene bromide, and fully characterized. The deuterated biologically active bromfenvinphos is an important compound for the advancement of environmental degradation testing and some mass spectrometric studies.
EXAMINATION OF BY-PRODUCTS FORMED UPON REACTING TRIALKYL PHOSPHITES WITH 2,4-DICHLOROPHENACYLIDENE BROMIDE AS A MECHANISTIC PROBE OF PERKOW REACTION
Koziara, Anna,Mloykowska, Barbara,Majewski, Piotr,Sledzinski, Bogdan,Zwierzak, Andrzej
, p. 399 - 409 (2007/10/02)
Besides the expected O,O-dialkyl-O--2-bromovinyl phosphates the formation of their structural analogs devoid of bromine or having two bromine atoms at the terminal position of vinyl group along with α-alkoxy-β-bromo-2,4-dichlorostyrene, α-alkoxy-β,β-dibromo-2,4-dichlorostyrene, and 2,4-dichlorophenacyl bromide was observed in Perkow reactions between trialkyl phosphites and chromatographically pure 2,4-dichlorophenacylidene bromide.The total quantity of side products markedly increases with increasing polarity of solvent.The formation of all the above mentioned compounds can be plausibly explained by assuming an intimate or solvent separated ion-pair as a common intermediate.
REACTIONS OF 2,4- AND 2,6-DICHLOROPHENACYLIDENE HALIDES WITH TRIALKYLPHOSPHITES IN PROTIC SOLVENTS. DIRECT EVIDENCE FOR THE "ENOLATE ANION" PATHWAY
Mlotkowska, Barbara,Majewski, Piotr,Koziara, Anna,Zwierzak, Andrzej,Sledzinski, Bohdan
, p. 631 - 642 (2007/10/02)
The reactions of 2,6-dichlorophenacyl and 2,6-dichlorophenacylidene chlorides and bromides with trimethyl and triethyl phosphites have been investigated.The reactivity of 2,6-dichlorophenacylidene chloride and bromide towards trialkyl phosphites was compared with that of 2,4-dichlorophenacylidene chloride and bromide.The influence of methanol, acting as a model protic solvent, on the above mentioned processes has also benn investigated.The mechanism of Perkow reaction of sterically hindered α-haloketones with bulky substituents around the carbonyl center is discussed.
