CAAC-Based Thiele and Schlenk Hydrocarbons.
Carbenes
conjugation
dimerization
radicals
structure elucidation
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
20 Apr 2020
20 Apr 2020
Historique:
received:
10
12
2019
pubmed:
22
1
2020
medline:
22
1
2020
entrez:
22
1
2020
Statut:
ppublish
Résumé
Diradicals have been of tremendous interest for over a century ever since the first reports of p- and m-phenylene-bridged diphenylmethylradicals in 1904 by Thiele and 1915 by Schlenk. Reported here are the first examples of cyclic(alkyl)(amino)carbene (CAAC) analogues of Thiele's hydrocarbon, a Kekulé diradical, and Schlenk's hydrocarbon, a non-Kekulé diradical, without using CAAC as a precursor. The CAAC analogue of Thiele's hydrocarbon has a singlet ground state, whereas the CAAC analogue of Schlenk's hydrocarbon contains two unpaired electrons. The latter forms a dimer, by an intermolecular double head-to-tail dimerization. This straightforward synthetic methodology is modular and can be extended for the generation of redox-active organic compounds.
Identifiants
pubmed: 31960562
doi: 10.1002/anie.201915802
pmc: PMC7187164
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
6729-6734Informations de copyright
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
J Am Chem Soc. 1986 Sep 1;108(19):6004-11
pubmed: 22175364
Chem Sci. 2018 Jul 2;9(28):6107-6117
pubmed: 30090299
Science. 2002 Mar 8;295(5561):1880-1
pubmed: 11884750
Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2815-9
pubmed: 26804451
J Phys Chem A. 2012 Aug 23;116(33):8599-607
pubmed: 22889383
J Am Chem Soc. 2011 Oct 19;133(41):16342-5
pubmed: 21932848
J Org Chem. 2019 Jul 19;84(14):8899-8909
pubmed: 31187990
J Am Chem Soc. 2017 Dec 27;139(51):18488-18491
pubmed: 29227677
Angew Chem Int Ed Engl. 2016 Oct 4;55(41):12886-90
pubmed: 27628756
Angew Chem Int Ed Engl. 2003 Feb 24;42(8):921-4
pubmed: 12596178
J Am Chem Soc. 2015 Jun 17;137(23):7519-25
pubmed: 26011769
Chem Rev. 2013 Sep 11;113(9):7011-88
pubmed: 23883325
Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1634-7
pubmed: 25504531
J Chem Phys. 2019 Jun 21;150(23):234306
pubmed: 31228896
Angew Chem Int Ed Engl. 2019 Jun 17;58(25):8546-8550
pubmed: 30980458
J Am Chem Soc. 2013 Dec 18;135(50):18766-9
pubmed: 24304381
Chem Sci. 2019 May 9;10(22):5719-5724
pubmed: 31293757
Angew Chem Int Ed Engl. 2013 Feb 4;52(6):1801-5
pubmed: 23280727
Phys Chem Chem Phys. 2015 Jan 14;17(2):983-91
pubmed: 25410418
Chem Sci. 2016 Oct 19;7(10):6514-6518
pubmed: 27928491
Chem Commun (Camb). 2018 Feb 27;54(18):2186-2199
pubmed: 29423462
Chem Sci. 2018 Apr 24;9(22):4970-4976
pubmed: 29938024
Angew Chem Int Ed Engl. 2018 May 14;57(20):5838-5842
pubmed: 29668119
Angew Chem Int Ed Engl. 2002 Nov 4;41(21):4006-11
pubmed: 12412065
Acc Chem Res. 2017 Aug 15;50(8):1997-2006
pubmed: 28731693
J Am Chem Soc. 2016 Sep 28;138(38):12648-54
pubmed: 27573478
Chem Sci. 2019 Feb 28;10(14):4077-4081
pubmed: 31049189
J Am Chem Soc. 2006 Feb 15;128(6):1812-7
pubmed: 16464079
Chem Rev. 2019 Nov 13;119(21):11291-11351
pubmed: 31593450
Acc Chem Res. 2014 Aug 19;47(8):2582-91
pubmed: 25068503
J Am Chem Soc. 2018 Feb 14;140(6):2206-2213
pubmed: 29342351
Angew Chem Int Ed Engl. 2014 Mar 10;53(11):2857-61
pubmed: 24497377
J Phys Chem B. 2012 Jan 26;116(3):1053-9
pubmed: 22185199
Angew Chem Int Ed Engl. 2017 Apr 24;56(18):5012-5016
pubmed: 28371126
Angew Chem Int Ed Engl. 2020 Apr 20;59(17):6729-6734
pubmed: 31960562
Chem Soc Rev. 2015 Sep 21;44(18):6578-96
pubmed: 25994857
J Am Chem Soc. 2016 Aug 17;138(32):10092-5
pubmed: 27479783
Org Lett. 2017 Oct 20;19(20):5605-5608
pubmed: 28968127
Angew Chem Int Ed Engl. 2019 Apr 23;58(18):6084-6088
pubmed: 30784151