Bromination of 'endo-benzocyclobutanorbornene': Synthesis of 'endo-11,12-dibromobenzocyclobutanorbornene': High-temperature bromination - Part XIV

Daştan, Arif; UZUNDUMLU, E; BALCI, M

Makale Tam Makale Uluslararası 2002

Bromination of 'endo-benzocyclobutanorbornene': Synthesis of 'endo-11,12-dibromobenzocyclobutanorbornene': High-temperature bromination - Part XIV

Arif Daştan, E UZUNDUMLU, M BALCI

HELVETICA CHIMICA ACTA Cilt 85 · Sayı 9 · ss. 2729–2739 · 01.01.2002

Özet

The electrophilic addition of Br to 'endo-benzocyclobutanorbornene' 5 at -50degrees led in high yield to the formation of the rearranged dibromides 6 and 7. However, high-temperature bromination of 5 in decalin at 150degrees gave exclusively nonrearranged product 8 in 98% yield. From the elimination of nonrearranged product 8, 'endo-bromobenzocyclobutanorbornene' 9 and 'endo-benzocyclobutanorbornene' 5 were obtained. Similarly. bromination of monobromide 9 at 77degrees yielded the nonrearranged tribromide 12 in quantitative yield. The dehydrobromination of 12 provided the 'endo 11,12-dibromobenzocyclobutanorbornene' 3 in high yield, which is a synthon for the trimerization reactions.

Atıf için künye

Daştan, A., UZUNDUMLU, E., & BALCI, M. (2002). Bromination of 'endo-benzocyclobutanorbornene': Synthesis of 'endo-11,12-dibromobenzocyclobutanorbornene': High-temperature bromination - Part XIV. HELVETICA CHIMICA ACTA, 85(9), 2729–2739.

BibTeX

@article{dastan2002-70694,
  author = {Daştan, Arif and UZUNDUMLU, E and BALCI, M},
  title = {Bromination of 'endo-benzocyclobutanorbornene': Synthesis of 'endo-11,12-dibromobenzocyclobutanorbornene': High-temperature bromination - Part XIV},
  journal = {HELVETICA CHIMICA ACTA},
  year = {2002},
  volume = {85},
  number = {9},
  pages = {2729--2739},
  issn = {0018-019X},
  url = {https://akademik.atauni.edu.tr/yayinlar/70694-bromination-of-endo-benzocyclobutanorbornene-synthesis-of-endo-1112}
}