Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions

CRESPO ANDRADA K. F., PEISINO L. E., GUNEY M., DAŞTAN A., PIERINI A. B.

ORGANIC & BIOMOLECULAR CHEMISTRY, cilt.11, sa.6, ss.955-965, 2013 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 11 Sayı: 6
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1039/c2ob26768c
  • Dergi Adı: ORGANIC & BIOMOLECULAR CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.955-965
  • Atatürk Üniversitesi Adresli: Evet

Özet

The photoinitiated substitution reactions of anti-7-bromobenzonorbornadiene (5), its syn isomer 6, exo-anti-13-bromobenzocyclobutanorbornene (7), syn-7-bromonorbornene (8) and bromonorbornane (9) with Me3Sn- and Ph2P- anions, in liquid ammonia, are here informed to occur with good yields of substitution. The stereochemical outcome is discussed in terms of calculations with the B3LYP functional and the 6-31+G* basis set; the solvent being included as a continuum through the PCM model. The experimental relative chemical reactivity of pairs of substrates toward a given anion is also presented.