Evidence map›Paper›PMID 30379070›Full record

ArticleJournal of the American Chemical Society2018

Controlling, Understanding, and Redirecting the Thermal Rearrangement of 3,3-Dicyano-1,5-enynes.

Sarah K Scott, Jacob N Sanders, Katherine E White, Roland A Yu, K N Houk, Alexander J Grenning

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Journal of the American Chemical Society, 2018. 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
–field-weighted citation impact
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.

  1. Article
  2. Article
  3. Vicinal stereocentersChemical science · 2023
    Article
  4. Article
  5. Article
  6. Article
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

6 authors.

Sarah K ScottDepartment of Chemistry , University of Florida , P.O. Box 117200, Gainesville , Florida 32611 , United States.
Jacob N SandersDepartment of Chemistry and Biochemistry , University of California-Los Angeles , 607 Charles E. Young Drive East , Box 951569, Los Angeles , California 90095-1569 , United States.
Katherine E WhiteDepartment of Chemistry , University of Florida , P.O. Box 117200, Gainesville , Florida 32611 , United States.
Roland A YuDepartment of Chemistry and Biochemistry , University of California-Los Angeles , 607 Charles E. Young Drive East , Box 951569, Los Angeles , California 90095-1569 , United States.
K N HoukDepartment of Chemistry and Biochemistry , University of California-Los Angeles , 607 Charles E. Young Drive East , Box 951569, Los Angeles , California 90095-1569 , United States.ORCID 0000-0002-8387-5261
Alexander J GrenningDepartment of Chemistry , University of Florida , P.O. Box 117200, Gainesville , Florida 32611 , United States.ORCID 0000-0002-8182-9464

Funding

Acquisition of a Q Exactive HF Hybrid Quadrupole-OrbitrapS10OD021758 · OD · UNIVERSITY OF FLORIDA · PI BASSO, KARI B · 2017 to 2017
$600k
Development of New Methods for Computational Enzyme DesignF32GM122218 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI SANDERS, JACOB NATHAN · 2017 to 2019
$176k
NIGMS NIH HHS F32 GM122218NIH HHS S10 OD021758
6 · The paper itself

Abstract

The thermal [3,3] rearrangement of 3,3-dicyano-1,5-enynes to γ-allenyl alkylidenemalononitriles (the "enyne Cope rearrangement") has largely eluded synthetic value as the desired products, too, are thermally reactive and ultimately yield 6π electrocyclization products. Herein, we describe experimental and computational studies related to the thermal rearrangement of 1,5-enynes, structural features to halt the thermal rearrangement at the allene stage, and a reductive variant for preparing bifunctional allenyl malononitriles. We also describe various ways that the bifunctional building blocks can be manipulated and converted to cyclic and acyclic architectures.

Identifiers

PMID30379070
PMCPMC6679653

What OpenQuestion holds

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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.