AN INVESTIGATION ON THE REACTIONS OF NAPHTHO[B]CYCLOPROPENE

SARACOGLU N., DURUCASU İ., BALCI M.

TETRAHEDRON, cilt.51, sa.40, ss.10979-10986, 1995 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 51 Sayı: 40
  • Basım Tarihi: 1995
  • Doi Numarası: 10.1016/0040-4020(95)00653-p
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.10979-10986
  • Atatürk Üniversitesi Adresli: Evet

Özet

In order to investigate the reactivity of naphtho[b]cyclopropene (2), the reaction with various diencphiles, dienes and electrophiles was examined. Reaction of 2 with tetracyanoethylene, 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione, 1,3-diphenylisobenzofuran and benzyne afforded the insertion products 3, 4, 6, 10. Cheletropic addition of dichlorocarbene to 2 gave 1,1-dichloronaphtho[b]cyclobutene (II). Hydrolysis and reductive elimination of 12 provided naphtho[b]cyclobutenone (13) and naphtho[b]cyclobutene (13), respectively. Naphtho[b]cyclopropene reacted with the different electrophiles like acetic acid, HCl, maleic acid, iodine, bromine, ethanol, and hydrogen afforded the corresponding ring-opening products 14, 15, 16, 17, 18, 19, 20 and 21, respectively.