Cyclohexene-4,5-dicarboxylic acid anhydride

When 1,2,3,6-tetrahydrophthalic anhydride (4-cyclohexene-l,2-dicarboxylic acid anhydride) (36) is heated with a mixture of hydrogen sulfide and hydrogen in the presence of cobalt sulfide, it gives octahydrobenzo[c]thiophene (53%) and a trace of 4,5,6,7-tetra-hydrobenzo[c]thiophene.48 Similar treatment of hexahydrophthalic anhydride gives a mixture (69%) of cis- and (rcww-octahydrobenzo[c]-thiophene, which may be separated by VPC.48... 

This adduct, 3-frimethyl,silyl-4-cyclohexene-l,2-dicarboxylic acid anhydride, and derived allylsilancs (5) and (d) wore roiiiul U> undergo some inleresting... 

The experiment that follows involves the conversion of 4-cyclohexene-cis-1,2-dicarboxylic acid (3) to cyclohexane-cis-l,2-dicarboxylic acid (4), as shown in Equation 17.8. The catalytic hydrogenation of 3 is considered to be selective because the carboxylic acid groups, -CO2H, are not reduced under the reaction conditions. The starting material for this reduction may be readily prepared by the hydrolysis of 4-cyclohexene-czs-l,2-dicarboxylic acid anhydride, which is the product of the Diels-Alder reaction between butadiene and maleic anhydride, according to the procedure outlined in Section 12.3, Part Cl. 

EXPERIMENT 14 Diels-Alder Reaction 4-Cyclohexene-c/s-1,2-dicarboxylic Acid Anhydride 257 6-89. In reference to question 6-88a ... 

Diels-Alder Reaction 4-Cyclohexene-cis-1,2-dicarboxylic Acid Anhydride... 

Figure 6.29 IR spectrum 4-cyclohexene-cts-l,2-dicarboxylic acid anhydride.

In general, on going from the unsaturated fuUy conjugated anhydrides to the saturated systems, the two C—O stretching modes begin to coalesce, and in many cases only a single band is observed. In maleic anhydride, these modes occur at 1060 and 899 cm whUe in ds-4-cyclohexene-l,2-dicarboxylic acid anhydride they are found at 998 and 935 cm . Explain this observation. 

If in Experiment [14] you had prepared the other possible diastereomer of the product, 4-cyclohexene-frans-l,2-dicarboxylic acid anhydride, how many lines would you expect to see in the NMR spectrum Note that this isomer does not have a mirror plane of symmetry. 

The preparation of 4-cyclohexene- s-l,2-dicarboxylic acid anhydride by the reaction of 1,3-butadiene with maleic anhydride is recorded ... 

The spectrum of 4-cyclohexene-cfs-l,2-dicarboxylic acid anhydride (Figure 8.33) is much less complex. Because of fhe mirror plane of symmetry in the compound, there are only four different carbon atoms and thus only four lines are seen in the fully decoupled NMR spectrum. This simplicity makes it easy to detect isomeric or other impurities in this sample. These impurities were not as easy to detect in the NMR spectrum. The 1 1 1 triplet... 

Figure 8.32 The NMR spectrum of 4-cyclohexene-cis-l,2-dicarboxylic acid anhydride in CDCI3.

Diels, Otto Fhul Hermann, 258-259, 270 Diels-Alder reaction, 257-275 bicyclic adduct, 454 carbocyclic rings, 454- 55 as cycloaddition reaction, 259 4-cyclohexene-ds-l,2-dicarboxylic acid anhydride, 257-268 defined, 259... 

Incorporation of an alicyclic dianhydride 5-(2,5-dioxotetrahydrofurfuryl)-3-methyl-3-cyclohexene-l,2-dicarboxylic acid anhydride (DOCDA, 98% purity), produced by Merck, Darmstadt, Germany (Matsumoto 1999)... 

As a result, two composite systems derived from partially aliphatic polyimides— 5-(2,5-dioxotetra-hydrofurfuryl)-3-methyl-3-cyclohexene-l,2-dicarboxylic acid anhydride reacting with 4,4 -oxydianiline (DOCDA-ODA) and with iron oxide as Fe304—were prepared at different temperatures, 250 and 300°C (Nica et al. 2015). Correlations among the structural, morphological, thermal, and magnetic properties were established for possible application as humidity sensor devices. In addition, the influence of humidity on the electrical properties of poly(DOCDA-ODA)/iron oxide composite were discussed, which led to an analysis of the humidity sensitivity of pure polyimide and of a poly(DOCDA-ODA)/Fe304 with different filler contents of iron oxides at various values of relative humidity (RH). 

Tetrahydrobenzyl alcohol (( )3-cyclohexenene-l-methanol) and 30% aqueous hydrogen peroxide were purchased from Fluka, AG. 3-Cyclohexene-1-carboxylic acid and cis-4-cyclohexene-l,2-dicarboxylic acid were used as purchased from Lancaster Chemical Co. Methyl iodide, acetic anhydride, Oxone (potassium peroxymonosulfate), Aliquot 336 (methyl tri-n-octylammonium chloride), sodium tungstate dihydrate and N,N-dimethylaminopyridine (DMAP) were purchased from Aldrich Chemical Co. and used as received. 3,4-Epoxycyclohexylmethyl 3, 4 -epoxycyclohexane carboxylate (ERL 4221) and 4-vinylcyclohexene dioxide were used as purchased from the Union Carbide Corp. (4-n-Octyloxyphenyl)phenyliodonium hexafluoroantimonate used as a photoinitiator was prepared by a procedure described previously (4). 

Eevulinic acid, see Aniline Malaoxon, see Malathion Malathion diacid, see Malathion Malathion dicarboxylic acid, see Malathion Malathion monoacid, see Malathion Malathion a-monoacid, see Malathion Malathion p-monoacid, see Malathion 2-Nitrophenol p-Malathion monoacid, see Malathion Malathion monocarboxylic acid, see Malathion Maleic acid, see 2-Chlorophenol, Maleic anhydride. Maleic hvdrazide. 4-Nitrophenol, Phenol Malonic acid, see Cyclohexene, 1,4-Dioxane Malonic acid semialdehyde, see irans-1,3-Dichloropropylene... 

Cyclohexanedicarboxylic acid, diethyl ester, CIS-, 29 Cyclohexanone, 90 4-Cyclohexene-I, 2-dicarboxylic ACID, diethyl ester, CIS-, 29 4-Cyclohexene-1,2-dicarboxylic anhydride, CIS-, 93... 

Cyclohexene-1-acetonitrile, 31, 25, 26 4-Cyclohexene-1, 2-dicarboxylic ACID, DIETHYL ester, cis-, 30, 29 4-Cyclohexene-1,2-dicarboxylic ANHYDRIDE, cis-, 30, 93 Cyclohexene oxide, 32, 39, 40 Cyclohexene sulfide, 32, 39... 

Cyclohexene-1,2-dicarboxylic acid. See Tetrahydrophthalic anhydride Cyclohexene, 1-methyl-4-(1-methylethenyl)-. See dl-Limonene... 

Synonyms 4-Cyclohexene-1,2-dicarboxylic acid Maleic anhydride adduct of butadiene 3a,4,7,7a-Tetrahydro-1,3-isobenzofurandione Tetrahydrophthalic acid anhydride 1,2,3,6-Tetrahydrophthalic anhydride [gD] Tetrahydrophthalic anhydride THPA Definition Commercial prod, is the cis-isomer Empirical CsHsOs Formula C,iH8(C0)20... 

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