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

Dastan, A; Uzundumlu, E; Balci, METİN

doi:10.1002/1522-2675(200209)85:9<2729::aid-hlca2729>3.0.co;2-#

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

Dastan A., Uzundumlu E., Balci M.

HELVETICA CHIMICA ACTA, cilt.85, sa.9, ss.2729-2739, 2002 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 85 Sayı: 9
Basım Tarihi: 2002
Doi Numarası: 10.1002/1522-2675(200209)85:9<2729::aid-hlca2729>3.0.co;2-#
Dergi Adı: HELVETICA CHIMICA ACTA
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.2729-2739
Orta Doğu Teknik Üniversitesi Adresli: Hayır

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.