109317-74-0Relevant articles and documents
Addition-Elimination Reaction in the Trifluoroacetylation of Electron-Rich Olefins
Moriguchi, Takeshi,Endo, Takeshi,Takata, Toshikazu
, p. 3523 - 3528 (1995)
Reactions of electron-rich olefins such as vinyl ether 1 and vinyl sulfide 2 with trifluoroacetic anhydride in carbon tetrachloride at room temperature proceeded by the formation of addition products 7 and 8, respectively, which were identified as stable intermediates by 1H NMR and IR spectra, eventually giving the corresponding trifluoroacetylated olefins 5 and 6 as substitution products.These reactions were also observed in chloroform and dichloromethane in the absence of base, such as pyridine.These results supported the addition-elimination mechanism.The processes of the addition and elimination were confirmed by the 1H NMR spectrum and kinetic study which led to the following results: The addition products 7 and 8 were formed through a stepwise trans addition, and the trifluoroacetylated olefins 5 and 6 were self-catalytically formed from the addition products 7 and 8 through Ei, E2, or E1, depending on the stability of the cationic intermediates 3 and 4.
Synthesis of trifluoromethyl-substituted 1,2,6-thiadiazine 1-oxides from sulfonimidamides under mechanochemical conditions
Bolm, Carsten,Julian Lentelink, Niklas,Rissanen, Kari,Sch?bel, Jan-Hendrik,Thomas Passia, Marco,Truong, Khai-Nghi
supporting information, p. 9470 - 9475 (2021/11/17)
TBS-protected or NH-sulfonimidamides react with β-alkoxyvinyl trifluoromethylketones under solvent-free mechanochemical conditions to give 3-trifluoromethyl-substituted three-dimensional 1,2,6-thiadiazine 1-oxides. C4-Functionalized products can be obtained by starting from cyclic enones and brominations of the initially formed heterocycles. The stability of the products was investigated by varying the pH value and storage under aerobic conditions. This journal is
Novel cycloaddition products from the reaction of 2,5-dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene with cycloalkenes, cyclodienes and cycloheptatriene, and of hexafluoroacetone azine with cycloheptatriene
Abdul-Ghani, Mohamad,Tipping, Anthony E.
, p. 5 - 11 (2007/10/02)
Thermal reaction (20-70 deg C) of the dichloroazine CF3CCI=N-N=CCICF3 (2) with cyclopentene (in CH2CI2 solwent), cycloheptene, indene, acenaphtylene, 2,3-dihydrufuran, 2,3-dihydropyran, norbornadiene, cyclopentadiene and dicyclopentadiene gives as the major product in each case the rearranged cycloadduct (3) containing a CF3CCI2 group; hydrolisys (CF3CCI2 --> CF3CO) to give the amide (4) takes place on attempted chromatographic purification on silica gel.With cyclopentene the rearrangad cyclopentadiene cycloadduct (3b) is also formed, while other products obtained by chromatographic separation from the 2,3-dihydropylan reaction are the 5,6-dihydropyran-3-yl azine (5), the hydrozone (8) and equimolar quantities of 5,6-dihydropyran-3-yl trifluoromethyl ketone (6) and the chlorohydrazone (7) possible arising via hydrolysis of the 1:2 adduct (16).The reaction of azine 2 with cycloheptatriene at 70 deg C gives a complex mixture, in which the major products are the rearranged cycloadduct (31) and the dehydrochlorinated cycloadduct (10) and (11) containing a CF3CHCI group.The corresponding reaction with hexafluoroacetone azine (1) at 70 deg C affords the criss-cross cycloadduct (22), the bis-ene adduct (23) and its oxidation product, the azo compound (24), and the cycloadduct diaziridine (25).