Gram‐Scale Synthesis and Highly Regioselective Bromination of 1,1,9,9‐Tetramethyl[9](2,11)teropyrenophane-Reference-Cited by-同舟云学术

Gram‐Scale Synthesis and Highly Regioselective Bromination of 1,1,9,9‐Tetramethyl[9](2,11)teropyrenophane

Published:2018-01-16 Issue:6 Volume:57 Page:1707-1711
ISSN:1433-7851
Container-title:Angewandte Chemie International Edition
language:en
Short-container-title:Angew Chem Int Ed

Author:

Unikela Kiran Sagar¹,Roemmele Tracey L.²,Houska Václav³,McGrath Kaitlin E.¹,Tobin David M.²,Dawe Louise N.⁴^ORCID,Boeré René T.²^ORCID,Bodwell Graham J.¹^ORCID

Affiliation:

1. Department of Chemistry Memorial University of Newfoundland St. John's NL A1B 3X7 Canada

2. Department of Chemistry University of Lethbridge 4401 University Drive Lethbridge AB T1K 3M4 Canada

3. Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic Flemingovo nám. 2 166 10 Prague 6 Czech Republic

4. Department of Chemistry and Biochemistry Wilfrid Laurier University 75 University Avenue W. Waterloo ON N2L 3C5 Canada

Abstract

AbstractAn improved synthetic pathway to the nanobelt‐like 1,1,9,9‐tetramethyl[9](2,11)teropyrenophane has been developed, and enables the synthesis of gram quantities of material. Key innovations are the development of a sequential chlorination/Friedel–Crafts alkylation reaction, a sequential iodination/Wurtz coupling reaction, and a room‐temperature teropyrene‐forming reaction. The teropyrenophane was found to form a very stable radical cation and undergo a completely regioselective fourfold bromination reaction.

Funder

Natural Sciences and Engineering Research Council of Canada

Publisher

Wiley

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201713067

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