An unprecedented Co-II-tetraphenylporphyrin-catalyzed decomposition of bicyclic endoperoxides: A new approach to substituted furofuran systems

2000-04-01
Sengul, ME
Simsek, N
Balcı, Metin
Co-II-tetraphenylporphyrin-catalyzed decomposition of bicyclic endoperoxides 4 and 5 with a strained double bond moiety has been studied. Compounds 4 and 5 have been synthesized by photooxygenation of 3 which itself was obtained by dichloroketene addition to cycloheptatriene, followed by removal of the chlorine atoms. An unusual decomposition mode of 4 promoted by Co-II-TPP resulted in the formation of 8 and 9 which are important building blocks in furofuran systems.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Suggestions

An investigation of the formation mechanism of allene or alkyne in the 6,7-benzobicyclo[3,2.1]octane system by deuterium labeling experiments
Taskesenligil, Y; Tumer, F; Kazaz, C; Balcı, Metin (1999-01-01)
In order to reveal the real intermediate in the base-promoted reaction of 1, 3-bromo-4,4-dideuterio-6,7-benaobicyclo[3.2.1]octa-2,6-diene 10 was synthesized and its HBr elimination reaction studied. Reaction of 10 with potassium tert-butoxide yielded butoxyl ether 18 in which proton-deuterium exchange has occured.
A novel asymmetric synthesis of highly enantiomerically enriched norbornane-type diamine derivatives
BOLM, CARSTEN; SCHİFFERS, INGO; ATODİRESEİ, IULİANA; Özçubukçu, Salih; RAABE, GERHARD (Royal Society of Chemistry (RSC), 2003-01-01)
The simple and highly enantioselective methanolysis of norbornene dicarboxylic acid anhydride mediated by quinidine leads to the corresponding cis-monomethyl ester with 98% ee. By means of selective ester epimerization, followed by Curtius degradation of the intermediate trans-diacyl azide, two optically active norbornane-type diamines are obtained as their hydrochloric salts. Liberating the amine with an excess of triethylamine in situ and subsequent derivatization affords potential C-1-symmetric ligands f...
The first enzymatic resolution of quaternary alpha-acetoxy alpha-substituted cyclic ketones
Tanyeli, Cihangir; İYİGÜN, Cigdem (Elsevier BV, 2006-04-03)
The enantioselective resolution of quaternary alpha-acetoxy alpha-substituted indanone and 1-tetralone derivatives was performed with commercially available enzyme CRL in pH = 8.0 phosphate buffer. Various parameters that would affect the enantoselectivities were tested, and the optimal enzymatic resolution condition was found to afford the enantiomerically enriched quaternary acetoxylated substrates with high ees (varied between 81% and 85%).
A theoretical study of the cycloaddition between cyclopentadiene and allylideneammonium cation: An AM1 study
Zora, Metin (2002-12-09)
The Diels-Alder reaction between cyclopentadiene and allylideneammonium cation has been studied by means of AMI semiempirical method. Allylideneammonium cation can add to cyclopentadiene via its either C=C or C=N bond. For each cycloaddition, four reactive channels have been characterized corresponding to the endo-s-trans, endo-s-cis, exo-s-trans and exo-s-cis approach modes. The results indicate that C=C bond of allylideneammonium cation is more reactive as dienophile than its C=N bond in reaction with cyc...
A new approach for one-pot, green synthesis of new polycyclic indoles in aqueous solution
Ameri, Mohsen; Asghari, Alireza; Amoozadeh, Ali; Bakherad, Mohammad (2017-05-01)
Electro-oxidation of phenylamine derivatives (1a and 1b) have been studied in the presence of pyrazolidine-3,5-dione (3) as a nucleophile in phosphate buffer solution mixed with ethanol, using voltammetric and spectroscopic techniques. The obtained results indicated that the oxidized form of phenylamines (2a and 2b) participate in Michael addition type reactions with pyrazolidine-3,5-dione (3) and via ECECCCCC mechanisms convert to the corresponding new polycyclic indoles (12a and 12b). In the present study...
Citation Formats
M. Sengul, N. Simsek, and M. Balcı, “An unprecedented Co-II-tetraphenylporphyrin-catalyzed decomposition of bicyclic endoperoxides: A new approach to substituted furofuran systems,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, pp. 1359–1363, 2000, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/55372.