Vinyl n-butyl ether

Diels-Alder reaction, of acrolein with B-butyl cyclohexenyl ether, n-butyl vinyl ether, and ethyl isopropenyl ether, 34, 30... 

Atkins et al. [130] reported in 1977 that irradiation of mixtures of benzene and methyl acrylate or methyl methacrylate, both acceptors, yields mixtures of endo and exo adducts. A subsequent report from the same groups [120] describes the results of the irradiations of benzene in the presence of ethyl vinyl ether, //-butyl vinyl ether, 2,3-dihydropyran, and 1,4-dioxene. In all these cases, the major products were exo-ortho photocycloadducts. The orientations of these vinyl ethers with respect to benzene, in their loose ground-state associations, were inferred from NMR spectra. For ethyl vinyl ether, n-butyl vinyl ether, 2,3-dihydropyran, and 1,4-dioxene, the vinyl proton resonances were either unaffected by a solvent change from carbon tetrachloride to hexadeuterobenzene or appeared 4-10 Flz downfield, whereas the methyl and/or methylene signals all moved up-field by 10-25 Hz. This implies an endo arrangement of the molecules in the ground state. Thus, the ortho photocycloadducts of vinyl ethers with benzene show exo stereochemistry, even when the ground-state orientation is endo. 

Butyl Vinyl Ether, Vinyl-N-Butyl Ether, N-Butyl Vinyl Ether Description Colorless liquid. 

Acid-catalyzed addition of aliphatic, aromatic or heteroaromatic cyanohydrins to ethyl vinyl ether, n-butyl vinyl ether or dihydro-4//-pyran provides base stable, protected cyanohydrin derivatives. Phase transfer catalyzed alkylation of aliphatic cyanohydrins with allylic bromides gave a-substituted a-allyl-oxyacetonitrile. Carbonyl compounds react wiA cyanide under phase transfer catalysis to give cyanohydrin anions, which are trapped by an acyl chloride or ethyl chloroformate to give acyl- or alkoxycarbonyl-protected cyanohydrins respectively. The reduction of the carbonyl group of an acyl cyanide by NaBH4 under phase transfer conditions followed by esterification serves as an alternative route to aldehyde-derived cyanohydrin esters. ... 

Dicyclopen tadiene, 32,41 36,33 37,65 Dicyclopropyl ketone, 38,19 Diels acid, 35, 38 Diels-Alder reaction, of acrolein with n-butyl cyclohexenyl ether, n-butyl vinyl ether, and ethyl iso-propenyl ether, 34, 30 of butadiene with maleic anhydride, 30, 93... 

Butyl vinyl ether. See n-Butyl vinyl ether n-Butyl vinyl ether... 

As an extension of this work, photoinduced [2-1-2]-cycloadditions of 1-acetyKsatin 13 with cyclic enol ethers (furan, benzofuran, 2-phenylfuran, 8-methoxypsoralen) and acyclic enol ethers (n-butyl vinyl ether and vinyl acetate) were investigated which afforded the spirooxetanes in high yields (82 to 96%)... 

Table 5. Reactivity Ratios in the Copolymerization of n-Butyl Vinyl Ether (Tfj) with Another Vinyl Ether (A ) ...

VINYL-n-BUTYL ETHER see BUTYL VINYL ETHER ... 

Cyclopropane 87, obtained from n-butyl vinyl ether, rearranges to dihydrofuran 88 only at elevated temperature, and also partly during work-up on silica gel113). The complete conversion of 87 into veratrole by the action of HCl/CH3OH gave rise to the analogous two-step synthesis of hydrourushiol monomethyl ether from l-diazo-3,3-dimethoxy-2-nonadecanone 89113). Ether cleavage of the product yields hydrourushiol, one of the vesicant components of, inter alia, poison ivy. 

For vinyl ethers, there again exists a strong preference for attachment of the formyl group to the carbon a to the oxygen atom. n-Butyl vinyl ether gave low yields of product, with the formyl group exclusively in the a position (4). 

Ferreira developed a novel method for the preparation of masked 1,4-dicarbonyl derivatives for utilization in the Paal-Knorr synthesis of pyrroles <00SC3215>. In this process, the reaction between diazocompound 3 and n-butyl vinyl ether using dirhodium tetraacetate as catalyst provides dihydrofurans 4 which are easily converted into substituted... 

Discuss the use of homogeneous versus heterogeneous reaction conditions for the coordination and traditional Ziegler-Natta polymerizations of propene, isoprene, styrene, methyl methacrylate, and n-butyl vinyl ether. 

Azadienes of this sort were studied simultaneously by Mariano et al., who reacted mixtures of (1 ,3 ) and (1E, 3Z)-l-phenyl-2-aza-l,3-pentadiene 275 with several electron-rich alkenes, e.g., enamines and enol ethers (85JOC5678) (Scheme 61). They found the (l ,3 )-stereoisomer to be reactive in this process affording stereoselectively endo 276 or exo 277 piperidine cycloadducts in 5-39% yield, after reductive work-up with sodium borohydride. The stereochemistry of the resulting adducts is in agreement with an endo transition state in the case of dienophiles lacking a cis alkyl substituent at the /8-carbon (n-butyl vinyl ether, benzyl vinyl ether, and 1-morpholino cyclopentene), whereas an exo transition state was involved when dihydropyrane or c/s-propenyl benzyl ether were used. Finally, the authors reported that cyclohexene and dimethyl acetylenedi-carboxylate failed to react with these unactivated 2-azadienes. 

It is reported that methyl acrylate, allyl acetate, vinyl acetate and dimethyl maleate give only low yields of oligomers with butyllithium under all experimental conditions (31). Furukawa and coworkers (32) confirm that vinyl acetate will not polymerize and that n-butyl-vinyl-ether will not either. High polymers can be formed from isopropyl acrylate (39) in toluene at —70° and from t-butyl acrylate (65). The reported failure of methyl acrylate and butyl acrylate to yield high polymers could reflect a genuine difference in behaviour connected with the side group or. could simply result from failure to choose the most favourable conditions for polymerization. Vinyl acetate can be polymerized by lithium metal (49) but co-polymerization experiments suggest that the polymer is formed by a radical mechanism. 

OtBu ( similar results to those of n-butyl vinyl ether structure of ortho adduct not published 12... 

Under comparable conditions the submitters found that the corresponding dihydropyran derivatives were similarly obtained by the condensation of acrolein with methyl vinyl ether in 80-81% yield, with ethyl vinyl ether (77-85% yield), with n-butyl vinyl ether (82% yield), with ethyl isopropenyl ether (50% yield), and with w-butyl cyclohexenyl ether (40% yield). Other a,j3-un-saturated carbonyl compounds that have thus been condensed with ethyl vinyl ether are crotonaldehyde (87% yield), meth-acrolein (40% yield), a-ethyl-/3- -propylacrolein (54% yield), cinnamaldehyde (60%yield), /3-furylacrolein (85%yield), methyl vinyl ketone (50% yield), benzalacetone (75% yield), and benzal-acetophenone (74% yield). 

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