Efficient rearrangement of epoxides catalyzed by a mixed-valent iron trifluoroacetate [Fe3O(O2CCF3)(6)(H2O)(3)]

Erturk, Erkan
Gollu, Mehmet
Demir, Ayhan Sıtkı
The mixed-valent oxo-centered triiron(III, III, II) trifluoroacetate complex [(Fe2FeO)-Fe-III-O-II(C2CCF3)(6)(H2O)(3)] Was prepared by reacting anhydrous iron(III) chloride with boiling trifluoroaceric acid under nitrogen. The non-hygroscopic and readily available mixed-valent triiron trifluoroacetate complex Was found to be an efficient catalyst for the regioselective rearrangement of epoxides. A number of carbonyl compounds formed via the rearrangement of epoxides could be obtained by a simple filtration of the reaction mixture through a short plug of silica gel.


A novel one-pot, three-component reaction for the synthesis of isocoumarin-condensed pyrazoles
OZCAN, Sevil; Dengiz, Çağatay; DELIOMEROGLU, Murat K.; ŞAHİN, Ertan; BALCI, METİN (Elsevier BV, 2011-03-30)
The one-pot, three-component reaction of substituted homophthalic anhydrides with hydrazine in DMF as solvent and reactant, at reflux temperature, afforded isochromeno[3,4-c]pyrazole-5(2H)-one derivatives in high yields. The mechanism and roles of the substrates were investigated and it was found that cyclic hydrazides were formed as intermediates.
Synthesis of various camphor-based chiral pyridine derivatives
Tanyeli, Cihangir; Isik, M (Elsevier BV, 2004-07-19)
(+)-beta-Hydroxymethylenecamphor 1 and enamines 2a-e were transformed into chiral camphor-based pyridine derivatives 3a-e via a tandem condensation reaction in good yields.
Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene
ÇALIŞKAN, Raşit; Nohut, Neslihan; Yilimaz, Ozlem; ŞAHİN, Ertan; Balcı, Metin (Elsevier BV, 2017-01-26)
Benzonorbornadiene and 7-oxabenzonorbornadiene were reacted with Meldrum's acid and dimethyl malonate in the presence of Mn(OAc)(3) and Cu(OAc)(2) in acetic acid. The reaction of benzonorbornadiene with Meldrum's acid gave a naphthalene derivative whereas the reaction with dimethyl malonate formed rearranged products derived from a carbocation intermediate. However, the reaction of 7-oxabenzonorbornadiene with Meldrum's acid gave two nonrearranged products. On the other hand, the reaction with dimethyl malo...
Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones
Demir, Ayhan Sıtkı; Aybey, Asuman (Elsevier BV, 2008-12-01)
The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords ph...
Synthesis of the possible carcinogenic dihydrodiol and diol epoxide of phthalazine
Ozer, G; Saracoglu, N; Menzek, A; Balcı, Metin (Elsevier BV, 2005-02-07)
Inverse-Diels-Alder reaction of dimethyl 1,2,4,5 -tetrazine-3,6-dicarboxylate with benzene cis-diol gave dihydrodiol coninini 2 the 1,4-dihydropyridazine ring. Attempts at oxidation of the dihydropyridazine ring with PIFA and MnO2, resulted in the formation of 5- and 5,6-dihydroxy-phthalazine derivatives. The oxidation of the dihydropyfidazine ring was achieved by way of photooxygenation. The phthalazine type dihydrodiol is unstable and easily undergoes aromatization. The Diels-Alder reaction of tetrazine w...
Citation Formats
E. Erturk, M. Gollu, and A. S. Demir, “Efficient rearrangement of epoxides catalyzed by a mixed-valent iron trifluoroacetate [Fe3O(O2CCF3)(6)(H2O)(3)],” TETRAHEDRON, pp. 2373–2377, 2010, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62767.