L- cyclooctene

The course of alkylation is also influenced by the steric arrangement of the enamine. 1-Pyrrolidino-l-cycloheptene gave approximately equal quantities of the C- and N-alkylated products in dioxane, while 1-pyrroli-dino-l-cyclooctene, and 1-pyrrolidino-l-cyclononene afforded N-alkylated products exclusively under similar eonditions (29). The reason for N alkylation in the eight- and nine-membered ring compounds is to be found in the conformation of these rings, which prevents full interaction of the unshared electrons on nitrogen with the n eleetrons of the double bond. 

Pure N-(l-cycloocten-l-yl)pyrrolidinc, b.p. 76-78° (1 mm.), may be isolated by distillation through a Vigreux column. 

The addition of ZnBi 2 to die tandem 1,3-azaprotio cyclotransfer-cycloaddition of a ketoxime with divinyl ketone results in rate enhancement and the exclusive formation of l-aza-7-oxabicyclo[3.2.1]octan-3-ones.79 The 1,3-dipolar cycloaddition of 1-aza-l-cyclooctene 1-oxide with alkenes produces the corresponding isoxazolidines in high yields with a minimum of polymeric material.80 The cycloaddition of thiophene-2 -carbaldehyde oxime with acetonitrile and methyl acrylate produces the 1,3-dipolar adduct, substituted isoxazolidines, and not the previously reported 4 + 2-adducts.81 Density functional theory and semi-empirical methods have been used to investigate the 3 + 2-cycloaddition of azoxides with alkenes to produce 1,2,3-oxadiazolidines.82 The 3 + 2-cycloaddition of a-nitrosostyrenes (62) with 1,3-diazabuta-l,3-dienes (63) and imines produces functionalized cyclic nitrones (64) regioselectively (Scheme 22).83... 

An interesting feature in this series, as well as in the corresponding unsubstituted 1,5-cyclooctadiyne (35) and l-cycloocten-5-yne (36) is the higher kinetic stability of... 

From these data it follows that increasing ring strain, i.e. smaller C C=C angles, generally leads to a shift to lower wave numbers. A linear correlation between wave numbers and experimental or calculated C C s C bond angles has been proposed 144) however some compounds, like l-cycloocten-4-yne, deviate significantly from the linear correlation. 

Little synthetic work has been reported on (p -alkene)2Fe(CO)3 complexes, with the exception of Fe(CO)3 ( l -cyclooctene)2. Grevels has shown this compound to be a versatile source of Fe(CO)3 in solution, and it has been nsed for that purpose. However, its use is far less common than other mild Fe(CO)3 transfer reagents such as (bda)Fe(CO)3 (Section 6.3.1). 

The L-cycloalkenes are also chiral. L-cyclooctene is a good example. Examination of the structures below using molecular models demonstrates that the two mirror images cannot be superimposed. 

In recent years, crosslinkable polymers have found a wide demand in the areas of interpenetrating polymer networks, non-linear optical materials, macro- and microlithography, and the formation of more thermally and chemically resistant materials. With this in mind, the controlled ROMP of 5-methacryloyl-l-cyclooctene (Scheme 8) was investigated to produce a linear polymer with cross-linkable methacrylate side chains. In addition, the copolymerisation of this monomer with cyclooctadiene (Scheme 9) allowed for the incorporation of a varying number of methacrylate side chains on the polymer backbone [23]. These copolymers were crosslinked through the methacrylate side chains with either thermal or photochemical initiation. Reaction of this multifunctionalised methacrylate polymer with methyl methacrylate under free radical polymerisation conditions led to the formation of AB crosslinked systems of poly(methyl methacrylate). A comparison of the... 

Dry diethyl malonate added to a soln. of Na in abs. ethanol, stirred 20 min. at 50° under N2, 5,6-epoxy-l-cyclooctene added, refluxed 3 days, aq. KOH added, and refluxed 1 hr. 10-oxo-9-oxabicyclo[6.3.0]undec-4-ene-ll-carboxylic acid (Y 70%) stirred 0.5 hr. at 80° with diethylamine and formalin soln., Na-acetate and glacial acetic acid added, and heated 15-30 min. at 80-90° 11-methylene-9-oxabicyclo[6.3.0]undec-4-en-10-one (Y 87%). F. e. s. N. Bensel, H. Marschall, and P. Weyerstahl, B. 108, 2697 (1975). 

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