Furfuryl chloride

Halogenomethyl, hydroxymethyl and aminomethyl groups readily undergo displacement reactions with nucleophilic reagents. Both side-chain and nuclear substitution products have been obtained (Scheme 57). These two possibilities are exemplified by the reaction of furfuryl chloride with sodium cyanide (Scheme 58). 

Furfural — see Furan-2-oarbaldehyde, 532 Furfuryl acetate, o -(butoxycarbonyl)-anodic oxidation, 1, 424 Furfuryi acrylate polymerization, 1, 279 Furfuryl alcohol configuration, 4, 544 2-Furfuryl alcohol polyoondensation, 1, 278 reactions, 4, 70-71 Furfuryl alcohol, dihydro-pyran-4-one synthesis from, 3, 815 Furfuryl alcohol, tetrahydro-polymers, 1, 276 rearrangement, 3, 773 Furfuryl chloride reactions... 

Furfuryl chloride, 35, 68 2-Furfuryl disulfide, 35, 68 S-2-Furfurylisothiourea, 35, 67 2-Furfuryl mercaptan, 35, 66 2-Furoic acid, 36, 36 Furylacrylic acid, 33, 25 Fusion, caustic, of vanillin, 30, 103... 

Thenyl chloride is more reactive than benzyl chloride. The rates of formolyses (ki x 104s-1) in 20% dioxane at 20 °C are as follows (75H(3)l) benzyl chloride, 0.85 2-thenyl chloride, 1.51 and furfuryl chloride, 695.0. The rates of reaction with various amines also increase in the same order. Normal replacement of the chlorine in 2-thenyl chloride by CN takes place in 30% aqueous MeCN with NaCN or KCN (conditions under which an abnormal product is exclusively formed with furfuryl chloride). 

Furfuryl mercaptan cannot be prepared according to the classical method using furfuryl chloride and potassium sulfide.2 It has been prepared by reduction of 2-furfuryl disulfide, obtained from furfural and ammonium hydrosulfide.3 The mercaptan has also been obtained in 33% yield 2 by the reaction of furfuryl chloride with thiourea and subsequent decomposition of the intermediate S-2-furfurylisothiourea according to the general method described in Organic Syntheses.4 In the present method, which has been published previously, the use of the very unstable and difficultly available furfuryl halides is avoided.6... 

Furfuryl chloride can undergo substitution by both SN2 and SN1 mechanisms. Since it is a 1° alkyl halide, we expect SN2 but not SN1 reactions. Draw a mechanism for the SN1 reaction shown below, with careful attention to the structure of the intermediate. How can this primary halide undergo SN1 reactions Why is there no competition with E2 or El mechanisms ... 

From Pd(DBA)2, 2-furfuryl chloride and PPhj the > -furfuryl complex XCIII can be isolated... 

Furans with suitable substituents in the 2-position can also be converted into phenols. These can be transformed into a 1,4-dicarbonyl system by 2,5 oxidation and ring opening. This system can then condense intramolecularly into a six-membered ring. The synthesis of m-hydroxybenzoic acid in 26% yield from furfuryl chloride is an example of this ... 

Cross-coupling of furfuryl chloride 305 with (indan-5-yl)pinacolylborane 306 gave benzylfuran 307 which was shown to be a modulator of AMPA receptor with... 

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