The effect of the double bond pyramidalization on the mode of the bromination reaction: Bromination of benzobicyclononadiene

BALCI, Metin; GUNEY, Murat; Daştan, Arif; AZIZOGLU, Akin

doi:10.1021/jo070253b

Makale Tam Makale Uluslararası 2007

The effect of the double bond pyramidalization on the mode of the bromination reaction: Bromination of benzobicyclononadiene

Metin BALCI, Murat GUNEY, Arif Daştan, Akin AZIZOGLU

JOURNAL OF ORGANIC CHEMISTRY Cilt 72 · Sayı 13 · ss. 4756–4762 · 22.06.2007

DOI ile aç

Özet

The bromination of 6,7,8,9-tetrahydro-5H-5,9-ethenobenzo[a][7]annulene yielded regio- and stereospecifically formed dibromides arising from the alkyl shift where the bromine exclusively attacks the double bond from the endo face of the double bond. DFT calculations on model compounds showed that the pyramidalization of the double bond and steric repulsion caused by the methylene protons are responsible for the stereo- and regioselective addition of bromine.

Atıf için künye

BALCI, M., GUNEY, M., Daştan, A., & AZIZOGLU, A. (2007). The effect of the double bond pyramidalization on the mode of the bromination reaction: Bromination of benzobicyclononadiene. JOURNAL OF ORGANIC CHEMISTRY, 72(13), 4756–4762. https://doi.org/10.1021/jo070253b

BibTeX

@article{balci2007-70734,
  author = {BALCI, Metin and GUNEY, Murat and Daştan, Arif and AZIZOGLU, Akin},
  title = {The effect of the double bond pyramidalization on the mode of the bromination reaction: Bromination of benzobicyclononadiene},
  journal = {JOURNAL OF ORGANIC CHEMISTRY},
  year = {2007},
  volume = {72},
  number = {13},
  pages = {4756--4762},
  issn = {0022-3263},
  doi = {10.1021/jo070253b},
  url = {https://akademik.atauni.edu.tr/yayinlar/70734-the-effect-of-the-double-bond-pyramidalization-on-the-mode-of-the-bromination}
}