Ethers cyclohexyl vinyl

A reversion of the addition direction has been observed in the case of electron rich alkenes such as enol ethers and enamines. For example, ethyl vinyl ether reacts with the mesoionic compound (9) to produce the cycloadduct (108) in 58% yield. Other examples are the reactions of mesoionic 1,3-dithiolones with cyclohexyl vinyl ether, cyclopenten-l-yl ethyl ether, ethyl isobuten-l-yl ether and /V-(isobuten-l-yl)morpholine. The observed regioselectivities have been also qualitatively discussed on the basis of MO perturbation theory (79LA360). 

Most alkenes do not polymerize in the presence of only hydrogen halides. One noticeable exception is JV-viny] carbazole, the most nucleophilic alkene, which is successfully polymerized by HI, HBr, and HC1 [111], Polymerization by HI produces well-defined polymers [112], Cyclohexyl vinyl ether also produces well-defined polymers when initiated by HI, although the polymerization is slow [113]. Other vinyl ethers form 1 1 a-alkoxyiodoethanes adducts with hydrogen iodide rather than polymer, especially in nonpolar solvents [Eq. (27)]. 

Nevertheless, bimolecular halide transfer [Eq. (106)] reportedly occurs in polymerization of cyclohexyl vinyl ether [113]. 

A similar effect was reported in polymerization of cyclohexyl vinyl ether (CHVE) initiated by HI alone [33]. The small addition (1%) of tetra-... 

In some systems it is necessary to add a large amount of salts to obtain polymers with low polydispersities. This happens when salts participate in ligand/anion exchange (special salt effect) and when they enhance ionization of covalent compounds through the increase of ionic strength. The special salt effect may either reduce or enhance ionization. Strong rate increases observed in the polymerization of isobutyl vinyl ether initiated by an alkyl iodide in the presence of tetrabutylammonium perchlorate or triflate can be explained by the special salt effect [109]. The reduction in polymerization rate of cyclohexyl vinyl ether initiated by its HI adduct in the presence of ammonium bromide and chloride can be also ascribed to the special salt effect [33]. The breadth of MWD depends on the relative rate of conversion of ion pairs to covalent species and is affected by the structure of the counterions. 

A further article of the same authors deals with the effect of a periodically reversed polarity on the electropolymerization of anethole, IBVE and cyclohexyl vinyl ether by I2 in DCE119. ... 

Chem. Descrip. Cyclohexyl vinyl ether CAS 2182-55-0 EINECS/ELINCS 218-561-7 Uses Diluent for cationic, charge transfer, and free radical radiation-curable coatings comonomer in specialty coatings mfg. monomer for tackifying adhesives... 

Bisphenol A diglyddyl ether Cyclohexyl vinyl ether... 

Rapi-Cure CHVE. See 1,4-Cyclohexanedimethanol divinyl ether Rapi-Cure CVE. See Cyclohexyl vinyl ether Rapi-Cure DDVE. See n-Dodecylvinyl ether Rapi-Cure DVE-2. See Diethylene glycol divinyl ether... 

Cyclohexyl vinyl ether Rapi-Cure CVE 2182-66-3 D5490... 

Figure 23-9. Titration of the alternating copolymer of maleic anhydride with ethyl, butyl, or cyclohexyl vinyl ethers in pure water at 30 C. (After P. L. Dubin and U. P. Strauss.)...

Other cationic systems studied include the polymerization of indene using tetrabutylammonium hexachloroantimonate in either dichloroethane or nitrobenzene. The antimonate was found to be more efficient and it was shown that polymerization occurred as a result of both direct oxidation of the monomer and by interaction with HSbCl, and HCIO4 produced electrochemically. Cerrai et al., investigating the polymerization of cyclohexyl vinyl ether, report that in dichloroethane with tetrabutylammonium perchlorate, only 0.05 mA was required to produce polymer by direct oxidation of the monomer. The same school, using cyclic voltammetry, rotating electrode voltammetry, and chromo-amperometry, report that the oxidation of anethole proceeds by an ECE mechanism with an intermediate chemical step of moderate velocity. 

Scheme 4.10 Domino carbonyl-ylide formation/l,3-dipolar cycloaddition reaction of a,a -dicarbonyl diazo compounds with cyclohexyl vinyl ether.

Scientists in basic cationic polymerisation chemistry have studied vinyl ethers for many years but, until recently, few monomers were available which gave products with useful properties e.g., triethylene glycol divinyl ether and cyclohexyl vinyl ether. Morflex has a range... 

The reaction was carried out by adding a solution of diazo substrate and cyclohexyl vinyl ether over a period of 1 h in dried and purified CH2CI2 with MeOH (10mol%) as an additive. 

For the BINlM-Ni(ll)-catalyzed reactions of cyclohexyl vinyl ether, the use of an epoxyindanone as the 3-acyl-2-benzopyrylium-4-olate precursor revealed that the chiral Lewis acid can function as a catalyst for asymmetric induction (Scheme 7.29). Thus, slow addition (over a period of 1 h) of epoxyindanone into a solution of cyclohexyl vinyl ether and the Ni(ll) catalyst in dry CH2CI2 under reflux conditions gave eniio-cycloadduct (60% yield) with 86% ee. This result suggests that the asymmetric induction is effectively catalyzed by the (7 )-BINIM-4Me-2QN-Ni(II) complex, and without the participation of Rh2(OAc)4, which may be involved only in the generation of the carbonyl ylides for reactions of diazocarbonyl compounds as substrates [66]. 

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