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Communication | Special issue | Vol 11, No. 1, 1978, pp.409-414
Published online, 1st January, 1970
DOI: 10.3987/S(N)-1978-01-0409
Stable 1H- and 2H-Isoindoles with Methyl Groups at the Carbocyclic System

Richard Kreher* and Karl Josef Herd

*Institut für Organische Chemie, Technische Hochschule Darmstadt, Petersenstrasse. 22 D-6100 Darmstadt, Germany

Abstract

4,5,6,7-Tetramethyl-2H-isoindole and 4,7- and 5,6-dimethyl-2H-isoindole are stable and isolable 10π-hetarenes, which can be prepared through a general and efficient route. The key step of the reaction sequence is the introduction of a cyclic carbon-nitrogen double bond via elimination of methanesulfinic acid. The spectroscopic properties of the tautomeric 2H- and 1H-isoindoles in solution and the chemical reactivity of the o-quinoid system towards dienophiles with an activated CC-double bond have been investigated and elucidated.