6π/10π-Electrocyclization of ketene-iminium salts for the synthesis of substituted naphthylamines
Tetrahedron Letters, cilt.55, sa.15, ss.2446-2449, 2014 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 55 Sayı: 15
- Basım Tarihi: 2014
- Doi Numarası: 10.1016/j.tetlet.2014.02.135
- Dergi Adı: Tetrahedron Letters
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.2446-2449
- Anahtar Kelimeler: DFT, Electrocyclization, Ketene-iminium salts, Naphthylamines
- Boğaziçi Üniversitesi Adresli: Evet
Özet
An intramolecular 6π/10π-electrocyclization from ketene-iminium salts was developed for the preparation of naphthylamines. Various substituents on the nitrogen, on the aromatic ring, and on the olefin were studied. Tricyclic skeletons were obtained in few steps and good overall yields. The electrocyclization of ketene-iminium salts has been computationally explored by means of DFT calculations and their activation barriers were compared to the parent triene as well as the corresponding dienyl allenes and dienyl ketenes. Electrocyclizations for ketene-iminium salts were shown to be highly exergonic and have much smaller barriers to activation. © 2014 Elsevier Ltd. All rights reserved.