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2-Furan acrylic acid

Furfural Pentose Furfuryl alcohol, furfuryl amine, furan-acrylic acid, tetrahydrofuran, levulinic acid, maleic anhydride Chheda etal., 2007 Corma etal., 2007... [Pg.88]

A concise, stereodivergent synthesis of ( )-cyclophellitol (380) and its unnatural diastereomer (17 , 15 )-cyclophelli-tol (379) starting from the furan/acrylic acid cycloadduct 375 was reported recently [136]. The key intermediate was the protected diol 377. For P = benzyl, the epoxidation with mCPBA is controlled by the free allylic hydroxyl group and led, after debenzylation, to (l/ , 15 )-cyclophellitol (379) (Scheme 13.81). A protection (TBSOTf)/debenzyla-tion sequence converted cyclohexenol 377 (P = PMB) into the silyl-protected diol 378. Selective epoxidation of this diol... [Pg.387]

From the Diels-Alder Adduct of Furan and Acrylic Acid. 29... [Pg.21]

The first three carba-sugars were synthesized by McCasIand and coworkers. Two other carba-sugars were prepared from myoinositol, and the remaining eleven carba-sugars have been synthesized from the Diels-Alder adduct of furan and acrylic acid. Conformational assignments of the carba-sugars were established with the aid of H-n.m.r. spectroscopy. [Pg.26]

The Diels-Alder cycloaddition of furan and acrylic acid, in the presence of hydroquinone as a polymerization inhibitor, provided enrfo-7-oxabicy-clo[2.2.1]hept-5-ene-2-carboxylic acid - (29) in a yield of 45%. Compound 29 was found to be the most accessible and important starting-material for the synthesis of various racemic carba-sugars, as well as their enantiomers. [Pg.29]

All sixteen of the racemic carba-sugars predicted are known, as well as fifteen of the enantiomers. The most accessible starting-material for the synthesis of racemic carba-sugars is the Diels-Alder adduct of furan and acrylic acid, namely, e i o7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylicacid (29). Furthermore, adduct 29 is readily resolved into the antipodes, (—)-29 and (+)-29, by use of optically active a-methylbenzylamine as the resolution agent. The antipodes were used for the synthesis of enantiomeric carba-sugars by reactions analogous to those adopted in the preparation of the racemates. [Pg.89]

Other 2-substituted cyclopropylideneacetates of type 3-X also entered this cycloaddition (Scheme 15) [19]. The endolexo selectivity is low but usually still higher than that of simple acrylic acid esters. The relative Diels-Alder reactivities of dienophiles 1-Me and 3-X as determined by competition experiments (Scheme 15) suggest a mechanism involving either diradicals or zwitterions as intermediates [19]. Surprisingly, the 2-fluoro derivative 3-F is less reactive than the parent compound 3-H. The 2-chloro and 2-bromo derivatives 1-Me and 3-Br have similar reactivities and cycloadd to furan (57) about 16 times faster than methyl acrylate. [Pg.164]

The corresponding reaction with 3-(3-furyl)acrylic acid also affords a mixture of 2-chloro-3-(3-furyl)acryloyl chloride (18%), 3-chlorothieno-[2,3-6] furan-2-carbonyl chloride (101) (25%), and 3,5-dichlorothieno-[2,3-6]furan-2-carbonyl chloride (102) [Eq. (32)]. [Pg.146]

All the theoretically predictable sixteen racemic pseudo-sugars have been synthesized, as well as the ten enantiomers. The most accessible starting material for the synthesis was the Diels-Alder adduct 33 of furan and acrylic acid. Furthermore, the adduct 33 was readily resolved by means of optically active a-methylbenzylamines into the two antipodes 86 and 87, which were also used for the preparation of enatiomeric pseudosugars. A chiral synthesis from true sugars was another prominent method for the preparation of the enantiomers. The remaining twenty two unknown enantiomeric pseudo-sugars will be prepared by either one of the two methods in the near future. [Pg.282]

A condensation occurs between 5-hydroxymethylfurfural and malonic ester20 and in a similar way, two molecules of malonic ester react with furan 2,5-dialdehyde.88 A condensation product, XXXV, has also been obtained with hydantoin.89 5-Hydroxymethylfurfural and its acetyl derivative undergo the Perkin reaction with sodium acetate and acetic anhydride giving 5-acetoxymethylfuran 2-acrylic acid (XXXVI).70 Similar products of the same reaction are obtained from 5-methyl-furfural71 and 5,5 -diformyl-l,l -furylmethyl ether (XXVII).61,72... [Pg.102]

Whereas 2-hydroxymethylthiophene reacts normally with hydrogen halides to give 2-halomethylthiophenes, reaction of 2-hydroxymethylfuran (furfuryl alcohol) with hydrochloric acid results in formation of levulinic acid 391 via the SN intermediate 390. The conversion of 3-(furan-2-yl)acrylic acid 392 into an ester of -oxopimelic acid 393 by ethanolic hydrochloric acid is a related reaction involving an analogous intermediate. [Pg.453]

SYNS AF-2 (presen-ative) FF FURYT-AMIDE FURYLFURAMIDE a-2-FURYL-5-NITRO-2-FURAN-ACYRLAMIDE 2-(2-FURYL)-3-(5-NITRO-2-FURYL)-ACRYLIC ACID AMIDE a-(FURYL)-P-(5-NITRO-2-FURYL)ACRYLIC AMIDE TOFURON... [Pg.685]

IDegradation. Heating of succinic acid or anhydride yields y-ketopimelic dilactone, cyclohexane-1,4-dione, and a mixture of decomposition products that include acetic acid, propionic acid, acrylic acid, acetaldeide, acrolein, oxalic acid, cyclopentanone, and furane. In argon atmosphere, thermal degradation of succinic anhydride takes place at 340°C (123). Electrolysis of succinic acid produces ethylene and acetylene. [Pg.537]

Xanthatin (3-methylene-7-methyl-6-[3-oxo-l-buten-l-yl]cyclohept-5-ene-[10,ll- ]furan-2-one, (-)-2-[(7/ )-7t-hydroxy-5c-methyl-4-(3-oxobut-l-en- -yl)cyclohept-3-en-r-yl)-acrylic acid lactone [26791-73-1] M 246,3, m 114.5-115 , [a] -20 (c 2, CHCI3), Crystalhse... [Pg.222]

Reactives of Side-Chains of Monocyclic Thiophens. - The rate constants for the esterification of some 3-, 4-, and 5-substituted thiophen-2-carboxylic acids and of some 2- and 4-substituted thiophen-3-carboxylic acids with diazodiphenylmethane in methanol solution have been measured, and linear correlations gave information about the transmission of substituent effects. The rates of alkaline hydrolysis of ethyl thiophen-2-carboxylate in ethanol-water and DMSO-water media have been measured and compared with those of other heterocyclic esters. The kinetics of iodination of 2-acetylthiophen in methanol-water, using different carboxylate buffers, have been studied.Basicity constants have been measured for j3-(2-thienyl)-acrylamides and compared with those of the corresponding benzene and furan derivatives. The acidity constants of ( )-a-phenyl-j3-(2-thienyl)-acrylic acids and analogous furan-, selenophen-, and pyridine-substituted compounds have been measured, and have been rationalized by an equation involving separate contributions of polar, conjugative, and steric effects of the heterocycles. ... [Pg.101]

Furan-2-acrylic acid H NMR, 4, 558 <65ACS485) Furan-2-carbaldehyde (furfural) dipole moment, 4, 555 (B-63MI31000, 65MI31001) AEa, 4, 543 (72T3015)... [Pg.23]

The known 7-e carboxylic acid 506, obtained by the condensation of acrylic acid with furan, was used as a substrate for synthesis of validamine, (510) a component of validamycin antibiotics. The treatment of 506 with hydrogen peroxide in formic acid gave the tricyclic compound 507, which after reduction and hydrolysis afforded cyclitol. Treatment of 508 with 2,2-dimethoxy-propane in the presence of an acid gave a mixture of diisopropylidene derivatives in which compound 509 was predominant. Introduction of an amino group, by way of a tosyl ester and azide displacement, followed by hydrogenation and hydrolysis, completed the synthesis of DL-val-... [Pg.215]


See other pages where 2-Furan acrylic acid is mentioned: [Pg.184]    [Pg.186]    [Pg.188]    [Pg.23]    [Pg.53]    [Pg.591]    [Pg.116]    [Pg.545]    [Pg.23]    [Pg.359]    [Pg.257]    [Pg.261]    [Pg.267]    [Pg.164]    [Pg.545]    [Pg.591]    [Pg.193]    [Pg.10]    [Pg.230]    [Pg.131]    [Pg.311]    [Pg.146]    [Pg.27]    [Pg.119]   
See also in sourсe #XX -- [ Pg.271 ]




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Furan acrylates

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