Chemistry Reference
In-Depth Information
10
SYNTHETIC APPLICATIONS OF
NITRENIUM IONS
D
UNCAN
J. W
ARDROP AND
E
DWARD
G. B
OWEN
10.1 Introduction
10.2 Electronic Structure of Nitrenium Ions
10.3 General Reactivity of Nitrenium Ions
10.3.1 Parent Nitrenium Ion
10.3.2 Alkyl Nitrenium Ions
10.3.3 Aryl Nitrenium Ions
10.3.4 Alkylaryl Nitrenium Ions
10.3.5 Heteroatom-Stabilized Nitrenium Ions
10.4 Parent Nitrenium Ion
10.5 Alkyl Nitrenium Ions
10.5.1 Early Studies and Proof of Existence
10.5.2 Cyclization of Unsaturated
N
-Chloramines (The Nitrenium Ion Question)
10.5.3 Ring Expansion and Contraction of Alkyl Nitrenium Ions (or Equivalents)
10.6 Aryl Nitrenium Ions
10.6.1 Early Studies: Bamberger Rearrangement and Proof of Existence
10.6.2 Generation from Aryl Azides and Cyclization
10.6.3 Cyclization to Carbazoles, Indoles, and Related
N
-Heterocycles
10.7 Heteroatom-Stabilized Acyl Nitrenium Ions
10.7.1 Generation and Intramolecular Aromatic Substitution
10.7.2 Application of
N
-Acyl Nitrenium Ion Annulation to Target-Directed Synthesis
10.7.3 Application of
N
-Acyl Nitrenium Ion Spirocyclization to Target-Directed Synthesis
10.8 Intermolecular Alkene Addition of Stabilized Nitrenium Ions
10.8.1 Alkene Addition of
N
-Stabilized Nitrenium Ions
10.8.2 Alkene Addition of
O
-Stabilized and Aryl Nitrenium Ions
10.9 Intramolecular Alkene Addition of Stabilized Nitrenium Ions
10.10 Conclusions and Outlook
Acknowledgments
References
