High-Temperature Bromination XIII [1]: Bromination of Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3dicarboxylate |
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Authors: | Şimşek Nermin Arici Cengiz McKee Michael L Ülkü Dinçcer Balci Metin |
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Institution: | (1) Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey;(2) Department of Engineering Physics, Hacettepe University, 06532 Ankara, Turkey;(3) Department of Chemistry, Auburn University, Auburn, Alabama, 36849;(4) Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey |
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Abstract: | The electrophilic addition of bromine to dimethyl 7-oxabicyclo2.2.1]hepta-2,5-diene-2,3-dicarboxylate 10 at 0 and –60°C led in high yield to the formation of dibromide 11. However, high-temperature bromination of 10 in carbon tetrachloride at 77°C gave four products 12–15, three of them with nonrearranged skeleton. Similarly, bromination of the dibromides 14 and 15 at 77°C yielded the nonrearranged tetrabromides 13 and 16, respectively. The structure of the tetrabromide 13 was solved by single-crystal X-ray analysis. The formation mechanism is discussed and supported by calculations. |
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Keywords: | Bromination high-temperature bromination dimethyl 7-oxabicyclo[2 2 1]hepta-2 5-diene-2 3-dicarboxylate |
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