Evidence map›Paper›PMID 31245793›Full record

ArticleARKIVOC : free online journal of organic chemistry

On the Winstein rearrangement: equilibrium and mechanism.

Amy A Ott, Joseph J Topczewski

Open access · diamondAbstract read
In one paragraph

Article in ARKIVOC : free online journal of organic chemistry. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing papers in PubMed
1.1field-weighted citation impact, top 27% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

6 citing papers in PubMed, 15 citations in OpenAlex.

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4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

2 authors at 1 institution in 1 country.

Amy A OttDepartment of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, United States.
Joseph J TopczewskiDepartment of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, United States.
University of Minnesota · US

Funding

Chiral α,α-Disubstituted Amine Synthesis by Dynamic Kinetic ResolutionR35GM124718 · NIGMS · UNIVERSITY OF MINNESOTA · PI TOPCZEWSKI, JOSEPH JOHN · 2017 to 2020
$1.5M
NIGMS NIH HHS R35 GM124718
6 · The paper itself

Abstract

Allylic azides are underutilized in organic synthesis when compared to other organic azides or other allylic functionality. This is likely because allylic azides rearrange at room temperature, resulting in a potentially complex mixture of azides. This rearrangement has been termed the Winstein rearrangement. Understanding the mechanism and basic principles governing the allylic azide equilibrium may aid in developing applications for these molecules based on either alkene or azide functionalization. Presented herein is a compilation of the key observations regarding the nature of the allylic azide rearrangement. Mechanistic considerations are explicitly addressed with key examples from the literature.

Indexed as

Azidesequilibriummechanismsigmatropic

Identifiers

PMID31245793
PMCPMC6594568
OpenAlexW2922942326

What OpenQuestion holds

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LicenceTDM
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.