From a 2,1‐Benzazaarsole to Elusive 1‐Arsanaphthalenes in One Step

The 2,1‐benzazaarsole (1) showed a diene‐like reactivity towards selected alkynes RC≡CR (R=CO2Me, C5F4N) thus forming 1‐arsa‐1,4‐dihydro‐iminonaphthalenes 2 a and 3 a as hardly isolable intermediates, that underwent facile CH→NH proton migration leading to before elusive substituted 1‐arsanaphthalen...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-04, Vol.25 (22), p.5668-5671
Main Authors: Kremláček, Vít, Erben, Milan, Jambor, Roman, Růžička, Aleš, Turek, Jan, Rychagova, Elena, Ketkov, Sergey, Dostál, Libor
Format: Article
Language:English
Subjects:
Alkynes
aromaticity
arsanaphthalenes
Chemistry
heterocycles
heterodienes
Intermediates
low valent compounds
Migration
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Summary:The 2,1‐benzazaarsole (1) showed a diene‐like reactivity towards selected alkynes RC≡CR (R=CO2Me, C5F4N) thus forming 1‐arsa‐1,4‐dihydro‐iminonaphthalenes 2 a and 3 a as hardly isolable intermediates, that underwent facile CH→NH proton migration leading to before elusive substituted 1‐arsanaphthalenes 2 b and 3 b that could be completely structurally characterized. Heterocycles: Unprecedented reactivity of 2,1‐benzazaarsole, as a heterodiene, with alkynes is reported. This procedure unexpectedly produced examples of structurally authenticated 1‐arsanaphthalenes (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201900805