CYCLOOCTENE, 1-NITRO

CYCLOOCTENE, 1-NITRO-, 50, 84 CYCLOPENTANECARBOXALDEHYDE, 1-PHENYL-, 51, 24 Cyclopentane-1,3-dione, 52, 4 Cyclopentanones, 54, 32 CYCLOPENTYLAMINE, 1-PHENYL-,... 

CYCLOOCTENE, 1-NITRO, 50, CYCLOPROP ANECARBOXYLIC ACID, cii-2-PHENYL, 50, 94 Cyclopropenes, 50, 30... 

The purity of the infrared spectroscopy or by gas chromatography using an NMPN (3-nitro-3-methylpimelonitrile) column. A low injection port temperature is desirable (<200°). 

Die Bestrahlung von cis- 1-Nitro-cycloocten liefert das /ra/u-Isomere, das mit Cyclopen-tadien uber Diels-Alder-Reaktion als trans-2-Nitro-trkydo[8.2.1.01,9 tridec-l 1-en abgefan-gen wird3,4 ... 

Commercial triethylamine (Eastman Kodak Co.) was used without further purification. Stoichiometric amounts of triethylamine based on olefin produced poor yields of nitro olefins owing to the slow rate of elimination of the nitro nitrite compounds.3 A twofold molar ratio of triethylamine to olefin was sufficient to produce 1-nitro-1-octadecene from l-nitro-2-octadecyl nitrite in 92% yield.3 The same excess applied to the crude reaction product from cyclooctene and dinitrogen tetroxide resulted in only an 80% yield of 1-nitrocyclooctene. 

Cyclooctene trans- -iodo-4-nitro-E21e, 5180 (1,3-Dien + NaN02/I2)... 

A reaction between heteroaromatic nitrone, a-(5-nitro-2-imidazolyl)-jV methylnitrone and cyclooctene was reported.54... 

Attempted reactions of 7d with Ru3(CO)i2 in order to isolate a possible nitrene complex intermediately formed were unsuccessful [9], Thus, we can only speculate about the reaction mechanism. Formation of a nitrene complex analogous to compound 4 is a reasonable hypothesis. However, when the carbonylation of some organic nitro derivatives was conducted in c/.y-cyclooctene as solvent and with Ru3(CO)i2 as catalyst, nitrones have been detected among the products [14]. Under these conditions, the intermediate nitroso derivative reacts with the alkene solvent to yield the corresponding nitrone. The reaction of nitroso derivatives with alkenes is in fact one of the methods for the preparation of nitrones [28]. Thus it could be that in the case of the carbonylation of ortho-nitrostyrenes, the reaction follows the path depicted in Scheme 4 ... 

Evidence for the intermediate formation of nitrone species during the carbonylation of nitroarenes in e s-cyclooctene as solvent catalysed by Ru3(CO)i2 have been obtained [14], Moreover, zerovalent palladium species with nitrogen donor ligands have been shown to be active catalysts in the reductive carbonylation of organic nitro derivatives [41]. The hypothesis that an intermediate having the olefinic double bond coordinated to the metal is formed during the catalytic cycle is supported by the steric effect that has been observed in the case of p,p -dimethyl-o-nitrostyrene (7f) as substrate. Moreover, such an intermediate could explain why a pentaatomic indole nucleus is preferentially formed, even when a conjugated double bond is present in the olefinic chain ... 

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