Two sterically congested cycloalkenes (9 and 10), congeners of tetra-tert-butylethylene, were synthesized and characterized. Oxidation of the bicyclic 1,3-dithietane 8 with dimethyldioxirane (DMD) gave the endo,endo-disulfoxide 13, thermal isomerization of which to the endo,exo-disulfoxide 15 followed by oxidation with DMD gave the trioxide 18. Heating 18 in refluxing 1,3-dimethyl-2-imidazolidinone furnished 1,2-di-tert-butyl-3,3,5,5-tetramethylcyclopentene (9) in 69% yield by a 2-fold extrusion process. The reaction of the 1,6-diketone dihydrazone 23 with Se(2)Cl(2) gave the selenadiazoline 34 and the 1,3-diselenetane 35. Heating 34 at 115-130 degrees C gave 1,2-di-tert-butyl-3,3,6,6-tetramethylcyclohexene (10), a "didehydro" derivative of tetra-tert-butylethylene, in 43% yield. The C=C bond in 10 is strained in degree comparable to those of most strained alkenes reported so far.

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Die Lichteinwirkung auf Lösungen der Tetrahydrothiophene (I) in Gegenwart von TiCl4 läßt ein Gemisch aus den Aldehyden (II), seinen Acetalen (III) und den cyclischen Produkten (IV) entstehen.

The cleavage of the epoxides (I), (VI), or (IX) with various catalysts (II) is investigated.

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