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Thermal and photochemical reactions of 1,4-dithiine and derivatives

✍ Scribed by Klaus Gollnick; Herta Hartmann

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
240 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

Thermally, dithiines may react as dienophiles in [ 2 + 4] -cycloadditions. Photochemically, they afford [ 2+ 2 ] -cyclodimerization products in the absence of oxygen ; in its presence, they are degraded to CO2 and H2S among other photooxidation products. CT-complexes occur with tetracyanoethylene, maleic anhydrides and acetylenes, but no stable products are formed, neither thermally nor photochemically. Thermal reactions of cyclic thioenol ethers with tetracyanoethylene ( TCNE ) produce [ 2 + 2 ] -cycloadducts via deeply colored CT-complexes 1 ; with dimethyl acetylenedicarboxylate ( DA), yellowish CT-complexes and [ 2+ 3]-cycloadducts. i. e. sulfonium ylid intermediates are formed which undergo either a retro-cycloaddition to starting materials or a fragmentation to stable products 2 .

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