Cis-Octene

Dramatic shape selectivities in competitive olefin epoxidation was observed with picnic basket metalloporphyrins312 313 designed to exclude bulky axial ligands on one sterically protected porphyrin face. When oxidized with PhIO in acetonitrile in the presence of the rigid p-xylyl-strapped porphyrin, cis-2-octene reacted selectively versus ds-cyclooctene or 2-methyl-2-pentene, giving >1000 reactivity ratios.313,314 Some immobilized manganese(III) porphyrins proved to be as efficient as their homogeneous equivalents in epoxidation with PhIO.151,315... 

C8H16 cis-2-octene 7642-04-8 172.95 16.678 2 14972 C8H16 3-methyl-2-ethyl-1-pentene 3404-67-9 148.70 10.363 2... 

C7H16S heptyl mercaptan 1639-09-4 liquid 1.550 1 14892 C8H16 cis-2-octene 7642-04-8 gas 0.309 1... 

Naphthalene dioxygenase from P. putida strain FI is able to oxidize a number of halogenated ethenes, propenes, and butenes, and cis-2-heptene and cis-2-octene (Lange and Wackett 1997). Alkenes with halogen and methyl substituents at double bonds form allyl alcohols, whereas those with only alkyl or chloromethyl groups form diols. 

Collman et al. reported a series of picket basket porphyrins (Figure 1.14) which show extremely high shape selectivity (>1,000 for cis-2-octene vs cw-cyclooctene) and relatively high enantioselectivity in olefin epoxidation (ee around 70-85%) Chiral, binaphthyl straps between adjacent o-aminophenyl groups have afforded very good enantiomeric selectivities for styrene epoxidations. ... 

Internal octenes comprising 1-octene, 2.5% trans-2-octene, 25% cis-2-octene, 12% cis-3-octene, 9%, trans-3-octene, 29% cis-4-octene, 6% trans-4-octene, 17%. 

The relative rates of [Mo(CO)6]-catalyzed epoxidation of olefins by erf-butyl hydroperoxide in benzene were found to be in the order allyl chloride (0.1) 1-octene (1.0) < styrene (1.3) < 2-methyl-l-heptene (9) < cyclohexene (13) < cis-2-octene (14), norbornene (14) < 2-methyl-2-heptene (75). Thus, electron donation in the form of alkyl groups about the double bond accelerates the reaction rate whereas electron withdrawal tends to retard it [379]. 

For the epoxidation of cis-and trans-2-octenes, the configuration of the double bond has been retained in the corresponding epoxides. In competitive reactions, cis-2-octene has been oxygenated much faster than the trans isomer, with a cis/trans ratio of 11.5 1. This value is higher than those obtained for the other tungstate-H202... 

The interaction of alkyne complexes with protic acids has been the most thoroughly studied of electrophilic reactions. When these reactions proceed to organic products, alkenes are formed, often stereospecifically. Schwartz and co-workers have studied the reactions of Cp2MH(alkyne) complexes of the early transition metals, Ta (Labinger et al, 1974) and Nb (Labinger and Schwartz, 1975). These complexes gave cis alkenes exclusively in nearly quantitative yield when treated with strong acids, as exemplified by the formation of cis-2-octene from the tantalum-octyne complex. Since the... 

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