Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions
Özet
The photoinitiated substitution reactions of anti-7-bromobenzonorbornadiene (5), its syn isomer 6, exo-anti-13-bromobenzocyclobutanorbornene (7), syn-7-bromonorbornene (8) and bromonorbornane (9) with Me3Sn- and Ph2P- anions, in liquid ammonia, are here informed to occur with good yields of substitution. The stereochemical outcome is discussed in terms of calculations with the B3LYP functional and the 6-31+G* basis set; the solvent being included as a continuum through the PCM model. The experimental relative chemical reactivity of pairs of substrates toward a given anion is also presented.
Atıf için künye
CRESPO ANDRADA, K. F., PEISINO, L. E., GUNEY, M., Daştan, A., & PIERINI, A. B. (2013). Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions. Organic and Biomolecular Chemistry, 11(6), 955–965. https://doi.org/10.1039/c2ob26768c
BibTeX
@article{crespoandrada2013-70688,
author = {CRESPO ANDRADA, Karina F. and PEISINO, Lucas E. and GUNEY, Murat and Daştan, Arif and PIERINI, Adriana B.},
title = {Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions},
journal = {Organic and Biomolecular Chemistry},
year = {2013},
volume = {11},
number = {6},
pages = {955--965},
issn = {1477-0520},
doi = {10.1039/c2ob26768c},
url = {https://akademik.atauni.edu.tr/yayinlar/70688-nucleophilic-substitution-of-bromonorbornenes-and-derivatives-by-electron}
}