Journal of Organic Chemistry p. 1089 - 1092 (1987)
Update date:2022-08-04
Topics:
Pierini, A. B.
Baumgartner, M. T.
Rossi, R. A.
In the present paper we report the reactions of o-dihaloaromatic compounds with dithiolate ions as new cyclization reactions occuring by the SRN1 mechanism. o-Diiodo- and o-bromochlorobenzene react under photostimulation with 3,4-toluenedithiolate ion to give good yields (ca. 60percent) of the cyclic disubstituted compound 2-methylthianthrene.The reaction occurs to a lesser extent (ca. 20percent) when the substrate was 1-bromo-2-iodonaphthalene. 2,3-Dichloroquinoxaline reacts with the same nucleophile in the dark or in the presence of radical traps to give a 100percent yield of the cyclic disubstituted compound.The reaction of o-diiodobenzene with 1,2-ethanedithiolate gave a low yield of the cyclic compound benzo-1,4-dithiane.This decrease was explained in terms of fragmentation reactions of the proposed radical anions intermediates.
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