From a 2, 1‐Benzazaarsole to Elusive 1‐Arsanaphthalenes in One Step. Issue 22 (27th March 2019)

• Record Type: Journal Article
• Authors: Kremláček, Vít; Erben, Milan; Jambor, Roman; Růžička, Aleš; Turek, Jan; Rychagova, Elena; Ketkov, Sergey; Dostál, Libor
• Is Part Of: Chemistry. Volume 25:Issue 22(2019)
• Page Start: 5668
• Page End: 5671
• Publication Date: 2019-03-27
• Subjects: aromaticity -- arsanaphthalenes -- heterocycles -- heterodienes -- low valent compounds; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201900805
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The 2, 1‐benzazaarsole (1 ) showed a diene‐like reactivity towards selected alkynes RC≡CR (R=CO2 Me, C5 F4 N) 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. Abstract : 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).