Bromination of norbornene derivatives: synthesis of brominated norbornanes and norbornenes

Gueltekin, Demet Demirci
Balcı, Metin
The low and high temperature bromination of 7-bromobicyclo[2.2.1]hept-2-ene and 2,7-dibromobicyclo[2.2.1]hept-2-ene were studied and the possible role of a neighboring group participation in rearrangements was investigated. The formation mechanism of the isomers as well as the role of the substituent on the rearrangement were discussed. The structure elucidation of the formed compounds was achieved by NMR spectral data; particularly, the gamma-gauche effect was discussed in connection with the configuration of the bromine atoms.


High temperature bromination. Part 18: Bromination of benzonorbornadiene derivatives: Polybrominated benzonorbornenes and benzonorbornadienes
Dastan, A; Balcı, Metin (Elsevier BV, 2005-06-06)
The low and high temperature bromination reactions of bromobenzonorbornadiene derivatives were studied and the possible role of a neighboring group in rearrangements was investigated. New polybrominated benzonorbornadiene and benzonorbornene derivatives were synthesized. All compounds were characterized property Using NMR spectroscopy.
Bromination of 5-methoxyindane: Synthesis of new benzoindenone derivatives and ready access to 7H-Benzo[c]fluoren-7-one skeleton
TUTAR, Ahmet; BERKİL AKAR, KIYMET; Hark, Richard R.; Balcı, Metin (Informa UK Limited, 2008-01-01)
The photobromination of 5-methoxyindane and 5-methoxyindanone was studied at both high and low temperatures. 1,2,3-Tribromo-6-methoxyindene was easily synthesized by photolytic bromination of 5-methoxyindane at low temperature. 1,1,2,3-Tetrabromo-6-methoxyindene was obtained from the photobromination of 5-methoxyindan at 77 degrees C, which could then be easily converted to the 2,3-dibromo-6-methoxyindene by silver-supported hydrolysis. Photochemical bromination of 5-methoxy-1-indanone with N-bromosuccinimi...
Functionalization of saturated hydrocarbons. High temperature bromination of octahydropentalene. Part 19
Gunbas, DD; Algi, F; Hokelek, T; Watson, WH; Balcı, Metin (Elsevier BV, 2005-11-21)
The synthesis and thermal bromination of octahydropentalene was studied. The reaction afforded 1a,3a,4b,6b-tetrabromo-1,2,3, 4,5,6-hexahydropentalene (14) with remarkable regio- and stereospecificity. The structure of the product was determined by H-1 and C-13 NMR data and single X-ray structural analysis. The treatment of octahydropentalene with tenfold bromine gave the octabromopentalene derivative. The formation mechanism of the products is discussed.
Chemistry of dioxine-annelated cycloheptatriene endoperoxides and their conversion into tropolone derivatives: an unusual non-benzenoid singlet oxygen source
Dastan, A; Balcı, Metin (Elsevier BV, 2006-04-24)
The chemistry of two bicyclic endoperoxides, obtained by photooxygenation of 2,3-dihydro-7H-cyclohepta[1,4]dioxine and 2,3-dihydro-7H-cyclohepta[b][1,4]dioxin-7-one was investigated with the aim of synthesizing the respective tropolone derivatives. The reaction of these endoperoxides with base, thiourea and their thermolysis provided the desired tropolone derivatives in high yield. On the other hand, the thermolysis of the endoperoxide derived from 2,3-dihydro-7H-cyclohepta[b] [ 1,4]dioxin-7-one underwent a...
Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies
Ali, Mohamed Fadelalla; Caliskan, Rasit Ali; ŞAHİN, Ertan; Balcı, Metin (Elsevier BV, 2009-02-14)
Homobenzonorbornadiene and benzobarrelene were reacted with dimedone/acetylacetone and Mn(OAc)(3) in the presence of Cu(OAc)(2) in acetic acid. Mainly rearranged products having a [2.2.2]skeleton and the nonrearranged dihydrofuran derivatives were obtained. These observations clearly indicated that the second oxidation takes place before the cyclization reaction. Furthermore, intramolecular tandem oxidations were observed where unusually oxyl radicals attack the double bond to form the products. The mechani...
Citation Formats
D. D. Gueltekin, Y. TAŞKESENLİGİL, A. DAŞTAN, and M. Balcı, “Bromination of norbornene derivatives: synthesis of brominated norbornanes and norbornenes,” TETRAHEDRON, pp. 4377–4383, 2008, Accessed: 00, 2020. [Online]. Available: