Ozonolysis of tetrasubstituted ethylenes, cycloolefins, and conjugated dienes on polyethylene

Transformations of peroxide products of olefins ozonolysis

“…Yet this method is not suitable for a number of substrates, like the most tetrasubstituted ethylenes, monocyclic olefi n (save the 4-6-membered rings), some bicyclic olefi ns, and conjugated dienes. In this connection the ozonolysis of olefi ns was carried out on solid organic polymers [6,7]. The powdered polyethylene exceeds in chemoselectivity the silica gel.…”

Extremely facile ring inversion and rearrangement in fluorobicyclo[2.1.0]pentanes

“…This synthetic scheme was therefore discontinued. Incidentally, 2,3-dimethylnorbornene (the hydrocarbon analogue of 28) forms a stable, crystalline ozonide [24], but norbornene (the analogue of 30) yields an ozonide that decomposes at room temperature [25].…”

Ozonolyses of Cyclopolyenes Adsorbed on Polyethylene

“…2 Polyethylene (Microethene FN 500 from Serva Feinbiochemica, Heidelberg, Germany; spherical particles, maximum size 20 µm) was continuously extracted with ether for 24 h to remove soluble components. Subsequently, it was dried at room temperature and 10 −3 Torr for 24 h.…”

“…2 The dried polyethylene was placed into a round-bottom flask and admixed with so much of a diethyl ether that the resulting suspension could be stirred. Then the olefin was added, the mixture was stirred for ca.…”

“…However, it was very recently that Griesbaum et al have been able to prepare the ozonides of larger cyclic olefins and bicyclic olefins by application of the modified ozonolysis on polyethylene. 2 It has been shown that cycloaddition of carbonyl oxides with aldehyde, and hence ozonide formation, can be substantially faciliated by the ozonolysis of olefins adsorbed on powdered polyethylene, presumably due to restricted migration of the primary cleavage fragments. [3][4][5][6][7] We have now tried whether this mode of reaction can be extended to the ozonolysis of cyclopolyenes.…”