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Cyclooctenes

The Cyclooctene Isomerization. A reaction that attracted some attention in recent years is the cis-trans isomerization of cyclooctene [84]. The cis isomer is much less strained than the trans, but the latter is readily fonned upon direct photolysis and also upon photosensitization. In this case, two enantiomeric trans isomers are formed. The appropriate loop is a variation of that shown in Figure 14, as shown in Figure 34. This is a phase inverting i -type loop, that... [Pg.367]

A mixture of 0.20 mol of the adduct from cyclooctene and dibromocarbene (note 1) and 250 ml of dry diethyl ether was cooled to -65°C. A solution of 0.23 mol of ethyllithium (note 2) in 200 ml of diethyl ether (see Chapter II, Exp. 1) was added in 15 min with cooling between -60 and -50°C. The reaction was very exothermic (note 3). After the addition the cooling bath was removed and the temperature was allowed to rise to about -10°C and the reaction mixture was poured into 200 ml of ice-water. The aqueous layer was extracted twice with diethyl ether. After drying, the solvent was removed in a water-pump vacuum and the remaining liquid was distilled through a 40-cm Vigreux column. 1,2-Cyclononadiene, b.p. 62°C/22 mmHg, 1.5059, was obtained in 86 yield. [Pg.140]

Note 1. Prepared from cyclooctene, bromoform and KO-tert.-C/jHg (see Ref. 52) or... [Pg.140]

Make molecular models of (f) and (Z) cyclooctene and compare their H—C=C—H dihedral angles... [Pg.201]

Cycloalkenes that have trans double bonds m rings smaller than 12 mem bers are less stable than their cis stereoisomers trans Cyclooctene can be isolated and stored at room temperature but trans cycloheptene is not stable above -30°C... [Pg.221]

The reaction of thiocyanogen (N=CS—SC=N) with cis cyclooctene proceeds by anti addition... [Pg.278]

Cyclooctatetraene is relatively stable but lacks the special stability of benzene Unlike benzene which we saw has a heat of hydrogenation that is 152 kJ/mol (36 kcal/mol) less than three times the heat of hydrogenation of cyclohexene cycloocta tetraene s heat of hydrogenation is only 26 kJ/mol (6 kJ/mol) less than four times that of CIS cyclooctene... [Pg.450]

One of the butadiene dimeri2ation products, COD, is commercially manufactured and used as an intermediate in a process called FEAST to produce linear a,C0-dienes (153). COD or cyclooctene [931-87-3], obtained from partial hydrogenation, is metathesi2ed with ethylene to produce 1,5-hexadiene [592-42-7] or 1,9-decadiene [1647-16-1], respectively. Many variations to make other diolefins have been demonstrated. Huls AG also metathesi2ed cyclooctene with itself to produce an elastomer useful in mbber blending (154). The cycHc cis,trans,trans-tn.en.e described above can be hydrogenated and oxidi2ed to manufacture dodecanedioic acid [693-23-2]. The product was used in the past for the production of the specialty nylon-6,12, Qiana (155,156). [Pg.344]

Another method that appears to have commercial potential is the ozonolysis of cyclooctene. Ozonolysis is carried out using a short chain carboxyHc acid, preferably propanoic acid, as solvent. The resultant mixture is thermally decomposed in the presence of oxygen at about 100°C to give suberic acid in about 60—78% yield (38—40). Carboxylation of 1,6-hexanediol using nickel carbonyl as catalyst is reported to give suberic acid in 90% yield (41). [Pg.62]

Dibenzo[a,d]cyclooctene, 5,6,7,12-tetrahydro-Dibenzo[a,d]cyclooctene, 5,6,7,12-tetrahydro-conformation, 7, 706... [Pg.600]

N-Acetyl-(R)-phanylalanlna (6). The rhodium catalyst was obtained by adding (-) dlop 5 (from diethyl tartrate) to a benzene solution of [RhCi(cyclooctene)2]2 under Ar, and stirring for tS mn A solution of the Rh catalyst (1 mM in EtOH PhH 4 1) was introduced under Hj to a solution of a-N acetylamino- phenytacrylic acid 4 (molar ratio Rh 4 1.540) The solvent was evaporated, the residue dissolved In 0 5 N NaOH, the catalyst was filtered and the solution acidified and concentrated to dryness to give 6 (81% ee) in 90 95% yield... [Pg.180]

The property of chirality is determined by overall molecular topology, and there are many molecules that are chiral even though they do not possess an asymmetrically substituted atom. The examples in Scheme 2.2 include allenes (entries 1 and 2) and spiranes (entries 7 and 8). Entries 3 and 4 are examples of separable chiral atropisomers in which the barrier to rotation results from steric restriction of rotation of the bond between the aiyl rings. The chirality of -cyclooctene and Z, -cyclooctadiene is also dependent on restricted rotation. Manipulation of a molecular model will illustrate that each of these molecules can be converted into its enantiomer by a rotational process by which the ring is turned inside-out. ... [Pg.82]

Molecules that are chiral as a result of barriers to conformational interconversion can be racemized if the enantiomeric conformers are interconverted. The rate of racemization will depend upon the conformational barrier. For example, -cyclooctene is chiral. E-Cycloalkenes can be racemized by a conformational process involving reorienting of the... [Pg.103]

E-Cyclooctene is also significantly straine4 but less so than -cycloheptene. As the ring size is increased, the amount of strain decreases. The. E-isomers of both cyclononene and cyclodecene are less stable than the corresponding Z-isomers, but for cycloundecene and cyclododecene, the E-isomers are the more stable. Table 3.10 gives data concerning the relative stability of the C7 through C12 cycloalkenes. [Pg.165]

Reaction of cyclooctene with trifluoroacetic acid occurs by a Itydride-shift process. [Pg.325]


See other pages where Cyclooctenes is mentioned: [Pg.368]    [Pg.115]    [Pg.120]    [Pg.201]    [Pg.201]    [Pg.201]    [Pg.221]    [Pg.256]    [Pg.261]    [Pg.450]    [Pg.469]    [Pg.545]    [Pg.588]    [Pg.272]    [Pg.272]    [Pg.426]    [Pg.429]    [Pg.430]    [Pg.380]    [Pg.153]    [Pg.153]    [Pg.155]    [Pg.75]    [Pg.181]    [Pg.181]    [Pg.70]    [Pg.70]    [Pg.104]    [Pg.166]    [Pg.359]   
See also in sourсe #XX -- [ Pg.228 ]

See also in sourсe #XX -- [ Pg.228 ]

See also in sourсe #XX -- [ Pg.74 , Pg.190 , Pg.199 , Pg.200 ]

See also in sourсe #XX -- [ Pg.228 ]

See also in sourсe #XX -- [ Pg.95 , Pg.97 , Pg.228 , Pg.496 ]

See also in sourсe #XX -- [ Pg.222 ]




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3-Trimethylsilyl-cyclooctene

4-Cyclooctene-l-carboxylic acid

Addition polymers cyclooctene

Alkene cyclooctene

Bicyclic cyclooctenes

Bicyclo nonane 5- cyclooctene

C/S-CYCLOOCTENE OXIDE

C/s-Cyclooctene

CATALYTIC SELECTIVE OXIDATION cyclooctene epoxidation

CYCLOOCTENE, 1-NITRO

Chiral compounds cyclooctene

Cis-CYCLOOCTENE OXIDE

Cis-cyclooctene

Copolymerization of cyclooctene

Cyclization cyclooctene

Cycloalkenes, photochemical cyclooctenes

Cyclohexan Cycloocten

Cyclooctatetraene Cyclooctene

Cycloocten

Cycloocten

Cyclooctene

Cyclooctene

Cyclooctene 1-methyl

Cyclooctene 2.2.2]cyclophane

Cyclooctene Subject

Cyclooctene addition of chlorine

Cyclooctene aldehyde

Cyclooctene chirality

Cyclooctene complex, with iridium

Cyclooctene complexes

Cyclooctene complexes manganese

Cyclooctene complexes palladium

Cyclooctene complexes silver

Cyclooctene copolymerization

Cyclooctene cross metathesis with

Cyclooctene cross-metathesis

Cyclooctene cyclic oligomers

Cyclooctene derivatives

Cyclooctene epoxidation

Cyclooctene epoxidation, catalysis

Cyclooctene extractable macrocyclics

Cyclooctene hydroformylation

Cyclooctene initial dissociation

Cyclooctene iridium-peroxo catalysts

Cyclooctene oxidation

Cyclooctene oxide

Cyclooctene oxides, transannular

Cyclooctene oxides, transannular reactions

Cyclooctene oxygen

Cyclooctene photoaddition reactions

Cyclooctene photochemistry

Cyclooctene photocycloaddition reactions

Cyclooctene photoisomerization

Cyclooctene polymerization

Cyclooctene propene

Cyclooctene racemization

Cyclooctene reaction with dibromocarbene

Cyclooctene ring opening metathesis polymerization

Cyclooctene solvolysis

Cyclooctene stability

Cyclooctene sulphide

Cyclooctene tethered

Cyclooctene trans stereoisomer

Cyclooctene with acetone

Cyclooctene with toluene

Cyclooctene, -: synthesis

Cyclooctene, catalytic dimerization

Cyclooctene, catalytic oxidation

Cyclooctene, chiral induction

Cyclooctene, conformation

Cyclooctene, epoxidation selectivity

Cyclooctene, epoxide

Cyclooctene, hydration

Cyclooctene, iridium and rhodium complexes

Cyclooctene, metathesis

Cyclooctene, platinum complex

Cyclooctene, reaction

Cyclooctene-4-carboxylic acid

Cyclooctene: hydroxylation

Cyclooctenes copolymerization

Cyclooctenes isomerization

Cyclooctenes ring-opening metathesis polymerization

Cyclopentene/cyclooctene, ROMP

C«-Cyclooctene

Dibenzo cyclooctene

Enantiodifferentiating photoisomerization of cyclooctenes

Epoxidation of cis-cyclooctene

Epoxidation of cyclooctene

Ethyl cyclooctene-2-carboxylate

Heat of hydrogenation cyclooctene

Hydrogen peroxide cyclooctenes

Irans-Cyclooctene

Isomerization, alkenes photochemical, cyclooctene

L- cyclooctene

Olefins cyclooctene

Photochemistry cyclooctene isomerization

Resolution of trans-cyclooctene

The cyclooctenes and their derivatives

Trans-Cyclooctene, chiral forms

Trans-cyclooctene

Z-cyclooctene

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