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Azides: their preparation and synthetic uses
Eric F. V. Scriven, and h Turnbull
Chem. Rev., 1988, 88 (2), 297-368• DOI: • Publication Date (Web): 01 May 2002
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Chemical Reviews is published by the American Chemical Society. 1155 Sixteenth
Street ., Washington, DC 20036
Chemical Reviews
Volume 88, Number 2 March/April 1988
Azides: Their Preparation and Synthetic Uses
ERIC F. V. SCRIVEN"
Reilly Tar & Chemical Corporation, Indianapolis, Indiana 46204
H TURNBULL'
Depaflment of Chemise, Wright State Universiiy, Dayton,, Ohio 45435
Received January 14, 1987 (Revised Manuscript Received June 9, 1987)
Contents B. Other Reductions 326
I. Introduction 298 C. Reductive Cyclizations 327
I I. Preparations 30 1 D. Curtius Reaction 329
A. From Halides 30 1 1. Thermal 329
1. By Displacement at Saturated Sites 30 1 2. Photochemical 330
2. With Rearrangement 303 E. Schmidt Reactlon 330
3. By Displacement at Unsaturated Sites 304 F. Staudinger Reaction 33 1
4. By Displacement at Atoms Other than 305 G. Amination 333
Carbon 1. By Reaction with Alkyl- or Aryllithium or 333
5. Via SR,l Reactions 305 Grignard Reagents
6. Thwarted Attempts 305 2. By Reaction with Alkenes and Related 334
B. From Sulfonates and Acetates 306 Species
C. From Epoxides 307 3. By Reaction with Boranes 334
D. From Ketais 308 4. Via Electrophilic Aromatic Substitution 335
E. From Alcohols 309 H. With Nucleophiles 335
F. From Carboxylic Acids 309 1. Carbon or Silicon Nucleophiles 335
G. From Alkenes 309 2. Nitrogen Nucleophiles 336
H. From pounds or Nitrates 312 3. Sulfur or Selenium Nucleophiles