68107-01-7Relevant academic research and scientific papers
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.
