Theoretical evidence for oxygenated intermediates in the reductive cyclization of nitrobenzenes
Organic Letters, cilt.6, sa.5, ss.743-746, 2004 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 6 Sayı: 5
- Basım Tarihi: 2004
- Doi Numarası: 10.1021/ol0364273
- Dergi Adı: Organic Letters
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.743-746
- Hacettepe Üniversitesi Adresli: Evet
Özet
Deoxygenation of nitroaromatics is a classic synthetic method for the construction of nitrogen heterocycles. The generally accepted mechanism involves exhaustive deoxygenation to a singlet nitrene. We present theoretical evidence for an alternative, 6π-electron 5-atom electrocyclization of nitroso-styrenes, -stilbenes, and -biphenyls to nitronates. A downstream 1,5-H shift and tautomerization leads to N-hydroxy heterocycles.