Propene, - 1-bromo 3-chloro-2-methyl

The results of the olefin oxidation catalyzed by 19, 57, and 59-62 are summarized in Tables VI-VIII. Table VI shows that linear terminal olefins are selectively oxidized to 2-ketones, whereas cyclic olefins (cyclohexene and norbomene) are selectively oxidized to epoxides. Cyclopentene shows exceptional behavior, it is oxidized exclusively to cyclopentanone without any production of epoxypentane. This exception would be brought about by the more restrained and planar pen-tene ring, compared with other larger cyclic nonplanar olefins in Table VI, but the exact reason is not yet known. Linear inner olefin, 2-octene, is oxidized to both 2- and 3-octanones. 2-Methyl-2-butene is oxidized to 3-methyl-2-butanone, while ethyl vinyl ether is oxidized to acetaldehyde and ethyl alcohol. These products were identified by NMR, but could not be quantitatively determined because of the existence of overlapping small peaks in the GC chart. The last reaction corresponds to oxidative hydrolysis of ethyl vinyl ether. Those olefins having bulky (a-methylstyrene, j8-methylstyrene, and allylbenzene) or electon-withdrawing substituents (1-bromo-l-propene, 1-chloro-l-pro-pene, fumalonitrile, acrylonitrile, and methylacrylate) are not oxidized. 

Propanone, 1-phenyl- [Benzyl methyl ketone), 55,94 Propene, 0 >l-bromo- 55, 108 Propene, (Z)-l-bromo- 55, 108 Propene, (F) 1 chloro-, 55, 104 Propene, (Z) 1 chloro, 55, 107 2-PROPENENITRILE, 2-(l,l-dimcthylethyl)... 

Elimination followed by nucleophilic addition to a strained C-C double bond was the main reaction sequence observed when a 1 3 mixture of (2-bromo-5-methyltetracy-clo[3.2.0.0 . 0 ]hept-l-yl)methanol and (7-bromo-5-methyltetracyclo[3.2.0.0 .0 ]hept-l-yl)methanol was allowed to react with a large excess of lithium aziridide. The main product, identified as 2-(aziridin-l-yl)-5-methyltetracyclo[3.2.0.0 -. 0" ]hept-l-yl methanol (13) and isolated in 21% yield, most likely results from aziridide attack on the intermediate lithium 5-methyltetracyclo[3.2.0.0 .0" ]hept-2(7)-en-l-yl)methoxide at C2. ° The other main product, 3-(aziridin-l-yl)-l-methyl-4-oxatetracyclo[4.3.0.0 .0 ]nonane (14), which was isolated in 15% yield, conceivably originates from the same intermediate as outlined above. Acyclo-propene intermediate was probably also formed when l-chloro-5-methyl-exo-6-phenyl-3-oxabicyclo[3.1.0]hex-2-one reacted with lithium 2,2,6,6-tetramethylpiperidide (LTMP) and gave 5-methyl-e.vo-6-phenyl-l-(2,2,6,6-tetramethyl-l-piperidyl)-3-oxabicyclo[3.1.0]hex-2-one (15) in 66% yield. 

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