High temperature bromination. Part 18: Bromination of benzonorbornadiene derivatives: Polybrominated benzonorbornenes and benzonorbornadienes

Dastan, A
Balcı, Metin
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.


High temperature bromination. Part 22: Bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b] naphthalene
Demirci-Gueltekin, Demet; Guenbas, Duygu D.; TAŞKESENLİGİL, Yavuz; Balcı, Metin (Elsevier BV, 2007-08-20)
The high-temperature bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b] naphthalene and its carboethoxy derivative was studied. Reaction of the title compound with 1 mol of bromine in refluxing carbon tetrachloride resulted in the formation of ring-opening products. In the case of the carboethoxy derivative,bromination took place both regio- and stereospecifically at the benzylic positions,the cyclopropane ring did not undergo bond cleavage. A mechanism for the formation of the products and their dehydrob...
High temperature bromination. Part 12: Bromination of 7-oxabenzonorbornadiene: Synthesis of 2,3-dibromo-7-oxabenzonorbornadiene
Altundas, A; Dastan, A; McKee, MM; Balcı, Metin (Elsevier BV, 2000-08-11)
The electrophilic addition of bromine to 7-oxabenzonorbornadiene (8) at 0 degrees C led in high yield to the formation of dibromoaldehyde 10. However, high-temperature bromination of 8 in carbontetrachloride at 77 degrees C gave non-rearranged products 17 and 18. From the elimination of non-rearranged products, 2-bromo-7-oxabenzonorbornadiene (12) was obtained. Similarly, bromination of monobromide 12 at 77 degrees C yielded the non-rearranged tribromides 19 and 20 while bromination of 12 at 0 degrees C gav...
Bromination of norbornene derivatives: synthesis of brominated norbornanes and norbornenes
Gueltekin, Demet Demirci; TAŞKESENLİGİL, Yavuz; DAŞTAN, Arif; Balcı, Metin (Elsevier BV, 2008-05-05)
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...
Low and high temperature bromination of exocyclic dienes: high temperature bromination. Part 16
Horasan, N; Kara, Y; Azizoglu, A; Balcı, Metin (Elsevier BV, 2003-05-19)
The electrophilic addition of bromine to an exocyclic diene, 5,6-dimethylenebicyclo[2.2.1]hept-2-ene, in CCl4 at 0degreesC led to the formation of non-rearranged (73%) and rearranged products (27%). However, high temperature bromination of the exocyclic diene at 77degreesC suppressed the formation of the rearranged products. Similarly, bromination of 9,10-dimethylenetricyclo[]undeca-2,4,6-triene at -10degreesC gave only the exo-1,2-addition product. Bromination at +5degreesC resulted in the form...
One-pot synthesis of N-substituted 2-methyl-4,5,6,7-tetrahydroindole derivatives
Tanyeli, Cihangir; Yazicioglu, EY (Elsevier BV, 2004-12-20)
We describe the preliminary results of one-pot syntheses of various N-substituted 2-methyl-4,5,6,7-tetrahydroindole derivatives from 2-(2-bromoailyl)cyclohexanone and the corresponding primary amines in good yields. Aliphatic amines were directly converted to tetrahydroindoles, whereas aromatic amines needed an extra base treatment step to complete the transformation.
Citation Formats
A. Dastan and M. Balcı, “High temperature bromination. Part 18: Bromination of benzonorbornadiene derivatives: Polybrominated benzonorbornenes and benzonorbornadienes,” TETRAHEDRON, pp. 5481–5488, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56908.