Structure of a ring enlarged product from the base induced rearrangement of dibromomethylenebenzonorbornene
Özet
The base-catalyzed rearrangement reactions of 2-bromomethylenebenzonorbornene 8 and 2,2-dibromomethylenebenzonorbornene 9 were studied. Reaction of 8 with potassium tert-butoxide in THF gave only the enol ether 11 whose formation is rationalized via a carbene-cycloalkyne mechanism. However, treatment of 9 with phenyllithium in THF at 40 degrees C gave the ring-enlarged dibromide 13 whose structure is reported herein. The ring-enlarged product 13 is rationalized in terms of carbanionic rearrangement. Quantum mechanical calculations are consistent with these observations.
Atıf için künye
BALCI, M., Krawiec, M., Taşkesenligil, Y., & Watson, W. H. (1996). Structure of a ring enlarged product from the base induced rearrangement of dibromomethylenebenzonorbornene. JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 26(6), 413–418. https://doi.org/10.1007/bf01665821
BibTeX
@article{balci1996-153039,
author = {BALCI, Metin and Krawiec, Mariusz and Taşkesenligil, Yavuz and Watson, William H},
title = {Structure of a ring enlarged product from the base induced rearrangement of dibromomethylenebenzonorbornene},
journal = {JOURNAL OF CHEMICAL CRYSTALLOGRAPHY},
year = {1996},
volume = {26},
number = {6},
pages = {413--418},
issn = {1074-1542},
doi = {10.1007/bf01665821},
url = {https://akademik.atauni.edu.tr/yayinlar/153039-structure-of-a-ring-enlarged-product-from-the-base-induced-rearrangement-of}
}