Prediction of the Synthesis of Spiro Derivatives by Double Intramolecular Aromatic Electrophilic Substitution Using Reactivity Indices.

Clicks: 388
ID: 56904
2019
Article Quality & Performance Metrics
Overall Quality
Not rated
Combines reader engagement with the AI quality analysis. This article has not been analysed, so there is no overall score — reader engagement is measured and shown alongside.
AI Quality Assessment
Not analyzed
Readership in this journal
Emerging

Ranked #43 of 475 articles by views in ACS omega

Most read Least read

Bar heights use a square-root scale. Only the 120 most-read articles are drawn; the journal has 475 in total.

Mint this article as an NFT
Not yet minted

Create a permanent, verifiable on-chain record of this article on the Scimatic Network. The NFT is held in your Journament account, and you can withdraw it to your own wallet at any time.

5 SUSD one-off · no wallet required
Sign in to mint
Abstract
The synthesis of heterocyclic spirobifluorene (SBF) analogs generally requires long and complicated synthetic pathways. Despite this synthetic effort, such structural modification allows the (opto)electronic properties of this remarkable three-dimensional node to be tuned especially for molecular electronic applications. For this reason, the development of a simple, robust, and efficient synthetic methodology to introduce various heterocycles in place of classical phenyl rings in the spirofluorene motif is highly and timely desirable. In this context, we describe herein our efforts to develop a straightforward and efficient synthesis leading to replacement of 2 phenyl rings by various heterocycles in spiro compounds from 2,2'-dibromobenzophenone. As the same procedure to form fully heterocyclic compounds failed, an original theoretical approach based mainly on the uncommon Fukui dual function was developed in order to determine clearly the limitation of this strategy and provide an efficient predictive tool. Indeed, such calculation allows prediction of the thermodynamic and kinetic aspects of the synthesis of spiro derivatives using a double aromatic electrophilic substitution. If this procedure reproduces well our experimental results focused on (heterocyclic) SBF compounds, it can be certainly adapted and generalized to other intramolecular substitutions.
Reference Key
dalinot2019predictionacs Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Dalinot, Clément;Jeux, Victorien;Sanguinet, Lionel;Cauchy, Thomas;Allain, Magali;Morille, Yohann;Bonnin, Valérie;Leriche, Philippe;
Journal ACS omega
Year 2019
DOI
10.1021/acsomega.8b03368
URL
Keywords
crystal structure hydrogen bonding n-heterocyclic carbene hirshfeld surface imidazolium salt

Citations

No citations found. To add a citation, contact the admin at info@scimatic.org

Comments

No comments yet. Be the first to comment on this article.