Literature DB >> 15547977

A slippery slope: mechanistic analysis of the intramolecular Scholl reaction of hexaphenylbenzene.

Pawel Rempala1, Jirí Kroulík, Benjamin T King.   

Abstract

DFT calculations support an arenium cation-based mechanism for the Scholl reaction converting hexaphenylbenzene to hexa-peri-benzocoronene. The curve connecting fully benzenoid intermediates on the potential energy diagram is convex. This "slippery slope" provides an explanation for the ease of this cascade Scholl reaction. The calculated reaction coordinate predicts that intermediates will not accumulate; this prediction is verified by experiment.

Entities:  

Year:  2004        PMID： 15547977     DOI： 10.1021/ja046513d

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  12 in total

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2.  Surface-assisted cyclodehydrogenation provides a synthetic route towards easily processable and chemically tailored nanographenes.

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3.  Polycyclic aromatic triptycenes: oxygen substitution cyclization strategies.

Authors:  Brett VanVeller; Derek J Schipper; Timothy M Swager
Journal:  J Am Chem Soc       Date:  2012-04-18       Impact factor: 15.419

4.  Synthesis of 2,24-Diene-12,13,15,16,34,35,37,38-octaphenyl[4.4]-triphenylparacyclophane.

Authors:  Bernard Wiredu; Mahendra Thapa; Sheen Y Hua; John Desper; Duy H Hua
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Authors:  Chitra R Edwankar; Rahul V Edwankar; Ojas A Namjoshi; Xuebin Liao; James M Cook
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

Review 7.  Atomically precise graphene nanoribbons: interplay of structural and electronic properties.

Authors:  R S Koen Houtsma; Joris de la Rie; Meike Stöhr
Journal:  Chem Soc Rev       Date:  2021-06-08       Impact factor: 54.564

8.  Controllable conversion of quasi-freestanding polymer chains to graphene nanoribbons.

Authors:  Chuanxu Ma; Zhongcan Xiao; Honghai Zhang; Liangbo Liang; Jingsong Huang; Wenchang Lu; Bobby G Sumpter; Kunlun Hong; J Bernholc; An-Ping Li
Journal:  Nat Commun       Date:  2017-03-13       Impact factor: 14.919

9.  Multiple-Porphyrin Functionalized Hexabenzocoronenes.

Authors:  Max M Martin; Dominik Lungerich; Frank Hampel; Jens Langer; Tanya K Ronson; Norbert Jux
Journal:  Chemistry       Date:  2019-10-22       Impact factor: 5.236

10.  Towards pi-extended cycloparaphenylenes as seeds for CNT growth: investigating strain relieving ring-openings and rearrangements.

Authors:  Thomas J Sisto; Lev N Zakharov; Brittany M White; Ramesh Jasti
Journal:  Chem Sci       Date:  2016-02-18       Impact factor: 9.825
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