Thia‐Aromaten, II. 1‐ und 2‐Thia‐naphthaliniumsalze

Abstract

Die unsubstituierten Grundkörper der Benzo‐thiopyryliumverbindungen, das 1‐ und das 2‐Thia‐naphthaliniumperchlorat sowie das 6.7‐Dimethoxy‐1‐thia‐naphthaliniumperchlorat werden auf mehreren Wegen erstmalig dargestellt, ihre chemischen Eigenschaften beschrieben, die Absorptionsspektren diskutiert.

Alkoxyoxindoles. A Convenient Method for the Reduction of Isatins

“…Chloroform solutions unless otherwise specified. 1 Methanol solutions 6. Deuteriochloroform solutions unless otherwise specified.…”

“…Abstraction of a hydride ion from C-6 of 6,11-dihydrobenz [6]indolo [2,3-<x]thiopyran (3a) with tntyl perchlorate gave an 88% yield of benz[b]indolo[2,3-d]thiopyrylium perchlorate (4a), and the 2-chloro-, 2-nitro-, and 2-, 8-, and 11-methylanalogs (4b-f, respectively) were similarly obtained in yields of 84-99%. The parent perchlorate salt 4a underwent ready metathesis with potassium iodide to form the corresponding thiopyrylium iodide 6.…”

“…spectral evidence suggested that the positive charge in these cations is localized predominantly on the sulfur atom rather than on the conjugated nitrogen atom. Reaction of the N-methyl compound 4f with phenylmagnesium bromide gave an adduct which was rearomatized with trityl perchlorate to 1 l-methyl-6-phenylbenz- [6]indolo [2,3-d]thiopyrylium perchlorate (8).…”