Allylic azides: synthesis, reactivity, and the Winstein rearrangement

Literature Information

Publication Date 2019-04-04
DOI 10.1039/C8OB03178A
Impact Factor 3.876
Authors

Angela S. Carlson, Joseph J. Topczewski


View Original

Abstract

Organic azides are useful synthetic intermediates, which demonstrate broad reactivity. Unlike most organic azides, allylic azides can spontaneously rearrange to form a mixture of isomers. This rearrangement has been named the Winstein rearrangement. Using allylic azides can result in low yields and azide racemization in some synthetic contexts due to the Winstein rearrangement. Effort has been made to understand the mechanism of the Winstein rearrangement and to take advantage of this process. Several guiding principles can be used to identify which azides will produce a mixture of isomers and which will resist rearrangement. Selective reaction conditions can be used to differentiate the azide isomers in a dynamic manner. This review covers all aspects of allylic azides including their synthesis, their reactivity, the mechanism of the Winstein rearrangement, and reactions that can selectively elaborate an azide isomer. This review covers the literature from Winstein's initial report to early 2019.

Related Literature

UV- and NIR-responsive polymeric nanomedicines for on-demand drug delivery

Gang Liu, Wei Liu, Chang-Ming Dong

2013-01-11 Review Article

DOI: 10.1039/C3PY21121E

Organoselenium compounds: development of a universal “living” free radical polymerization mediator

Jindong Zeng, Jian Zhu, Xiangqiang Pan, Zhengbiao Zhang, Nianchen Zhou, Zhenping Cheng, Wei Zhang, Xiulin Zhu

2013-04-19 Communication

DOI: 10.1039/C3PY00285C

Triphenylphosphine as phosphorus catalyst for reversible chain-transfer catalyzed polymerization (RTCP)

Liangjiu Bai, Lifen Zhang, Yuan Liu, Xiangqiang Pan, Zhenping Cheng, Xiulin Zhu

2013-03-04 Paper

DOI: 10.1039/C3PY00187C

Back cover

Cover

DOI: 10.1039/C3PY90027D

Contents list

2021-02-24 Front/Back Matter

DOI: 10.1039/C3PY90035E

SET-LRP synthesis of novel polyallene-based well-defined amphiphilic graft copolymers in acetone

Guolin Lu, Yongjun Li, Hao Guo, Weiyuan Du, Xiaoyu Huang

2013-03-05 Paper

DOI: 10.1039/C3PY00145H

Towards high-performance heterogeneous palladium nanoparticle catalysts for sustainable liquid-phase reactions

Beau Van Vaerenbergh, Jeroen Lauwaert, Pieter Vermeir, Joris W. Thybaut, Jeriffa De Clercq

2020-07-09 Review Article

DOI: 10.1039/D0RE00197J

You might also like

Compound Q&A

What is 1-(2,4,6-Trifluorophenyl)ethanol (CAS: 1250113-83-7)?

1-(2,4,6-Trifluorophenyl)ethanol is an organic compound with the CAS number 1250...

1250113-83-71-(2,4,6-Trifluoroph...
Compound Q&A

Is 1-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-2-pyrrolidinone (CAS: 919111-34-5) safe?

1-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-2-pyrrolidinone (CAS: 919111-34-5) is ...

919111-34-51-(2,4-Dimethoxybenz...
Compound Q&A

What are the physical and chemical properties of (7S,15R)-6β,15-Diacetoxy-7α,20-epoxy-7-hydroxykaura-2,16-dien-1-one (CAS: 51419-51-3)?

(7S,15R)-6β,15-Diacetoxy-7α,20-epoxy-7-hydroxykaura-2,16-dien-1-one is a crystal...

51419-51-3(7S,15R)-6β,15-Diace...
Compound Q&A

What regulatory guidelines apply to rac-ethyl (1r,4r)-4-hydroxycyclohexane-1-carboxylate, trans (CAS: 3618-04-0)?

The compound rac-ethyl (1r,4r)-4-hydroxycyclohexane-1-carboxylate, trans (CAS: 3...

3618-04-0rac-ethyl (1r,4r)-4-...
Compound Q&A

What is the market or research trend for 2-(2,4-Difluorophenoxy)-3-nitropyridine (CAS: 175135-62-3)?

The market for 2-(2,4-Difluorophenoxy)-3-nitropyridine (CAS: 175135-62-3) is cur...

175135-62-32-(2,4-Difluoropheno...
Compound Q&A

What are the main uses of 6-Diazo-5-oxo-L-norleucine (CAS: 157-03-9)?

The main uses of 6-Diazo-5-oxo-L-norleucine (CAS: 157-03-9) include research in ...

157-03-96-Diazo-5-oxo-L-norl...
Compound Q&A

What precautions should be taken when handling 2-Aminoethyl-mono-amide-DOTA-tris(tBu ester) (CAS: 173308-19-5)?

When handling 2-Aminoethyl-mono-amide-DOTA-tris(tBu ester) (CAS: 173308-19-5), i...

173308-19-52-Aminoethyl-mono-am...
Compound Q&A

How is 5-Methylimidazo[1,2-a]pyridine-3-carbaldehyde (CAS: 178488-37-4) typically synthesized?

5-Methylimidazo[1,2-a]pyridine-3-carbaldehyde (CAS: 178488-37-4) can be synthesi...

178488-37-45-Methylimidazo[1,2-...
Compound Q&A

Are there alternatives to 2,4,6-Trihydroxyisophthalaldehyde (CAS: 4396-13-8) in synthesis?

There are alternative reagents that can be used in the synthesis of 2,4,6-Trihyd...

4396-13-82,4,6-Trihydroxyisop...
Compound Q&A

What is (2Z)-3-(5-Fluoro-1H-indol-3-yl)-2-sulfanylacrylic acid (CAS: 179461-52-0)?

(2Z)-3-(5-Fluoro-1H-indol-3-yl)-2-sulfanylacrylic acid is a chemical compound wi...

179461-52-0(2Z)-3-(5-Fluoro-1H-...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.