Butyl vinyl ether tert

Microwave promoted, palladium-catalyzed, DPPP-controlled arylation of butyl vinyl ether with 4-tert-butylphenyl triflate afforded the branched arylation product and the corresponding methyl ketone, indicating the occurrence of selective internal a-arylation. Addition of water to the reaction mixture and microwave-heating for 2.8 min at 55 W smoothly produced the hydrolyzed product, 4-tert-butylacetophe-none, with an isolated yield of 77% (Eq. 11.2) [17]. 

Equation 11.2 Heck-coupling of 4-tert-butylphenyl triflate and butyl vinyl ether in the presence of water (DPPP = 1,3-bis (diphenyl phosphino) propane). 

Inspired by the previous results, Leighton et al. reported the enantioselective [3 + 2] acylhydrazone-enol ether cycloaddition reaction by employing the same pseudoephedrine-based chiral silane. The pyrazohdine product was obtained in 61% yield with 6 1 dr and 77% ee in 24 h. The use of tert-butyl vinyl ether led to an improvement in both diastereoselectivity and enantioselectivity as shown in Scheme 34 [108]. 

The inverse-electron demand 1,3-dipolar cycloaddition has also been pursued with other Ti(TV) complexes (364). The cycloaddition reaction of C,(V-diphenyl nitrone to tert-butyl vinyl ether catalyzed by different bidentate C2-symmetrical ligands gave moderate to good diastereoselectivity, and up to 41% ee was achieved. 

Both reactivity and selectivity decreased with increasing steric bulk of alkyl group on the vinyl ether (Et> -Pr> -Bu /-Bu), and tert-butyl vinyl ether was completely unreactive. The cycloaddition of ethyl vinyl ether with a wide variety of oc, 3-unsaturated aldehydes bearing aliphatic and aromatic P-substituents proceeded with high selectivity (>95% de, 89-98% ee). Only 5 mol% of catalyst were necessary except in the case of sterically more demanding substituents (R = i-Pr, Ar) that required 10 mol% of catalyst loading. Substitution could also be introduced in the a-position of the unsaturated aldehyde, and cycloadducts were obtained with similar high selectivities.26... 

C6H12CIN303 3-(2-chloroethyi)-1- 3-hydroxypropyl)-3-nitr 60784-47-6 387.90 33.227 1,2 8396 C6H120 tert-butyl vinyl ether 926-02-3 348.15 27.382 1.2... 

Problem 7.19 tert-Bulyl vinyl ether is polymerized commercially for use in adhesives by a cationic process. Draw a segment ofpoly( ert-butyl vinyl ether), and show the mechanism of the chain-carrying step. 

In the presence of catalytic amounts of p-toluenesulfonic acid, D-galactose diethyl dithioacetal (112) reacts248 with tert-butyl vinyl ether to afford the 5,6-O-ethylidene derivative 113 in 56% yield Wolfram and Parekh248 proposed that the reaction proceeds by initial, electrophilic addition of 0-6 to the double bond, followed by pro-... 

Dimethylethoxy)-2-methylpropane, 3072 t Butyl methyl ether, 2010 f tert-Butyl methyl ether, 2011 t Butyl vinyl ether, 2484 t Cyclopropyl methyl ether, 1608 t Diallyl ether, 2431... 

Vinyl butoxyethyl ether (ethylene glycol butyl vinyl ether) [4223-11-4] M 144.2, b 70-7 2 /20mm, d 0.866, n 1.4220, Wash the ether with aqueous 1% NaOH, dry with CaH2, then reflux with, and distil it from sodium. Stabilize it with 0.5% of 2,6-di-tert-butyl-p-cresol for storage. [Beilstein 1 IV 2387 ] IRRITANT. 

Thiault G., A. MeUouki, G. Le Bras Rate constants for the OH radical reaction with n-propyl, n-butyl, iso-butyl and tert-butyl vinyl ethers to be submitted (2005). 

Denizli, B. K., Can, H. K., Rzaev, Z. M. O., and Gitner, A. 2006. Synthesis of copolymers of tert-butyl vinyl ether with maleic and citraconic anhydrides. Journal of Applied Polymer Science 100 2453-2463. 

The present cation pool-initiated polymerization using a microflow system can be applied to other vinyl ethers such as isobutyl vinyl ether (IBVE) and tert-butyl vinyl ether (TBVE) (Table 14.2). The corresponding macroscale batch polymerization results in much poorer molecular weight distribution control. 

Iwasawa has reported the gold(III)-catalyzed reaction of N-(o-ethynylphenyl)imi-nes with electron-rich alkenes to form polycyclic indole derivatives [26]. As an example, reaction of N-[l-(l-pentynyl)phenyl]imine 28 and tert-butyl vinyl ether with a catalytic amount of AuBrs in toluene at room temperature led to isolation of the polycyclic indole 29 in 80% yield as a mixture of diastereomers (Scheme 11.3). Conversion of 28 to 29 presumably occurs via initial intramolecular hydroamination to form the gold carbene containing azomethine ylide 30 that undergoes intermo-lecular [3 + 2] cydoaddition with tert-butyl vinyl ether to form the carbene complex 31. 1,2-Migration of the 7t-propyl group to the metal-bound carbon atom coupled with deauration then forms 29. This transformation is also catalyzed efficiently by PtCl2 [26]. 

Products N-vinyl caprolactam, N-vinyl formamide, vinyl ethers, tert-butyle acrylate, butanediomonoacrylate, tertiary butyl methacrylate... 

Fig. 54a and b. ESR spectra with TM,g cavity of propagating radicals of tert-but vinyl ether and isobutyl vinyl ether at room temperature [TBPO] = 1.3 M. (a) tert-butyl vinyl ether, (b) isobutyl vii l ether... 

Zhou, Y. and Faust, R. (2003) Synthesis of poly(isobutylene-b-tert-butyl vinyl ether) and poly (isobutylene-b-tert-butyldimethylsHylvinyl ether) diblock copolymers. ACS Polym. Prepr. (Div. Polym. Chem.), 44(2), 661-662. 

Hallensleben s work with n-butyl (NBVE), isobutyl (IBVE), and tert-butyl vinyl ether (TBVE) copolymerization with MA shows the same effect. The copolymerization rates follow the order TBVE>IBVE > NVBE, with corresponding K values (table in appendix to this chapter) of 2.12, 1.11, and 0.56 liter mole ... 

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