The first and efficient synthesis of some of the polyhalogenated benzobarrelenes: unusual formation of a benzosemibullvalene derivative

ŞENGÜL, Mustafa; Gültekin, Demet; Eşsiz, SELÇUK; ŞAHİN, Ertan; DAŞTAN, Arif

doi:10.1016/j.tet.2009.04.034

The first and efficient synthesis of some of the polyhalogenated benzobarrelenes: unusual formation of a benzosemibullvalene derivative

ŞENGÜL M., Gültekin D. D., Eşsiz S., ŞAHİN E., DAŞTAN A.

Tetrahedron, cilt.65, sa.25, ss.4859-4865, 2009 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 65 Sayı: 25
Basım Tarihi: 2009
Doi Numarası: 10.1016/j.tet.2009.04.034
Dergi Adı: Tetrahedron
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.4859-4865
Anahtar Kelimeler: Benzobarrelene, Benzosemibullvalene, Bromination, Polybromides, Polychlorides, Polyhalogenides
Hakkari Üniversitesi Adresli: Hayır

Özet

New polyhalogenated benzobarrelenes were synthesized in good yields. The bromination reaction of benzobarrelenes at high temperature gives non-rearranged products. Dehydrobromination of the formed products with t-BuOK yielded the desired polyhalogenated benzobarrelenes. The elimination reaction of cyclopropanoid dibromide with a base unusually resulted in the formation of a benzosemibullvalene derivative. © 2009 Elsevier Ltd. All rights reserved.