A new cyclic telluride. Synthesis and reactions of 1,3,5,6,7,8-hexahydronaphtho[2,3-c]tellurophene

Abstract

Reaction of 6,7-bis(chloromethyl)-1,2,3,4-tetrahydronaphthalene with tellurium powder and potassium iodide in 2-butoxyethanol gave 2,2-diiodo-1,3,5,6,7,8-hexahydro-naphtho[2,3-c]tellurophene(1) as a red-orange solid in 40% yield. Reduction of 1 with hydrazine hydrate gave a pale yellow solid of 1,3,5,6,7,8-hexahydronaphtho[2,3-c]telluro-phene(2) in 80% yield. Chlorination, bromination of 2 and its reaction with benzyl bromide and N-bromosuccinimide were reported. 2,2-Bis(dimethyldithiocarbamato)-, 2,2-bis (diethyldithiocarbamato)- and 2,2-bis(piperidine-1-carbodithioate)-1,3,5,6,7,8-hexahydro-naphtho[2,3-c]tellurophene were prepared by the reaction of the corresponding sodium dithiocarbamate salt with 1. Mononuclear platinum complex (ie, [(C₁₂H₁₄Te)₂PtCl₂]) was obtained by the reaction of 2 with K₂PtCl₄. Reaction of 6,7-bis(chloromethyl)-1,2,3,4-tetrahydronaphthalene with KTeCN in DMSO solution gave 2,2-dihydroxo-1,3,5,6,7,8-hexahydronaphtho[2,3-c]tellurophene (11) as a white solid in 55% yield. All these new compounds were characterized by elemental analysis, IR, ¹H, and ¹³C NMR, and mass spectroscopic data.

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