High temperature bromination. Part 12: Bromination of 7-oxabenzonorbornadiene: Synthesis of 2,3-dibromo-7-oxabenzonorbornadiene
Özet
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 gave the rearranged product 11. The dehydrobromination of tribromides (19, 20) provided the 2,3-dibromo-7-oxabenzonorbornadiene (21), which is a synthon for the trimerization, in high yield (C) 2000 Elsevier Science Ltd. All rights reserved.
Atıf için künye
ALTUNDAS, A., Daştan, A., MCKEE, M., & BALCI, M. (2000). High temperature bromination. Part 12: Bromination of 7-oxabenzonorbornadiene: Synthesis of 2,3-dibromo-7-oxabenzonorbornadiene. TETRAHEDRON, 56(33), 6115–6120. https://doi.org/10.1016/s0040-4020%2800%2900561-5
BibTeX
@article{altundas2000-70720,
author = {ALTUNDAS, A and Daştan, Arif and MCKEE, MM and BALCI, M},
title = {High temperature bromination. Part 12: Bromination of 7-oxabenzonorbornadiene: Synthesis of 2,3-dibromo-7-oxabenzonorbornadiene},
journal = {TETRAHEDRON},
year = {2000},
volume = {56},
number = {33},
pages = {6115--6120},
issn = {0040-4020},
doi = {10.1016/s0040-4020(00)00561-5},
url = {https://akademik.atauni.edu.tr/yayinlar/70720-high-temperature-bromination-part-12-bromination-of-7-oxabenzonorbornadiene}
}