Unusual fragmentation of fulvene endoperoxides with phenyliodosyl bis(trifluoroacetate) (PIFA)

Ozer, G
Saracoglu, N
Balcı, Metin
Reaction of unsaturated fulvene endoperoxides with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate gave saturated fulvene endoperoxides containing the 1,2-dihydropyridazine ring. Treatment of dihydropyridazine endoperoxides with water followed by phenyliodosyl bis(trifluoroacetate) oxidation provided acrylic acid derivatives and dimethyl pyridazine-3,6-dicarboxylate.


Synthesis of 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives
Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005)
A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...
A facile synthesis of various butenolides
Tanyeli, Cihangir (Informa UK Limited, 2000-01-01)
The synthesis of alpha'-acyloxy-alpha,beta-unsaturated cyclic ketones from the corresponding alpha,beta-unsaturated cyclic ketones by using manganese (III) acetate in combination with 2-chloropropionic acid followed by subsequent Arbuzov and intramolecular Horner-Emmons cyclization reactions provided a convenient synthetic pathway to various butenolides 4a-d.
Synthesis and chemistry of unusual bicyclic endoperoxides containing the pyridazine ring
Ozer, G; Saracoglu, N; Balcı, Metin (American Chemical Society (ACS), 2003-09-05)
Inverse-Diels-Alder reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with unsaturated bicyclic endoperoxides gave the bicyclic endoperoxides containing the pyridazine ring. The NEt3 and CoTPP (TPP = tetraphenylporphyrin) catalyzed reaction of endoperoxide 8 resulted in the formation of hydroxy ketone 11 and cis-diol 9. Cleavage of the peroxide linkage in 8 with thiourea provided cis-diol 9. Oxidation of hydroxy ketone 11 and cis-diol 9 led to the phthalazine-5,8-dione 10. Furthermore, the various tr...
A new and short synthesis of 7H-benzo[a]cyclohepten-7-one and some derivatives: Oxidation of 7-bromo-5H-benzo[a]cycloheptene
Dastan, A; Yildiz, YK; Balcı, Metin (Informa UK Limited, 2001-01-01)
Oxidation of 7-bromo-5H-benzo[a]cycloheptene with some oxidation reagents has been studied. Several 2,3- and 4,5-benzotropone derivatives has been obtained. The structures of the products were determined by H-1-, (CNMR)-C-13 data and chemical transformation.
One-pot synthesis of chloroalcohols and their lipase mediated kinetic resolution - ferrocenyl aziridinylmethanols as chiral ligands in enantioselective conjugate diethylzinc addition to enones
İşleyen, Alper; Doğan, Özdemir; Department of Chemistry (2007)
An unexpected tricyclic ether formation instead of acetate addition to the double bond of a norbornene derivative aroused our interest to explore the mechanism of this reaction. Mechanistic studies showed that methylene diacetate (MDA) was formed in the stock solution (NBu4OAc + dichloromethane) and decomposed to formaldehyde under Lewis or Brønsted acid conditions. Formaldehyde and olefin condensation (Prins reaction) clearly explains the formation of the unexpected product. Same methodology was then succe...
Citation Formats
G. Ozer, N. Saracoglu, and M. Balcı, “Unusual fragmentation of fulvene endoperoxides with phenyliodosyl bis(trifluoroacetate) (PIFA),” JOURNAL OF HETEROCYCLIC CHEMISTRY, pp. 529–533, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56405.