2-Methyl-2-vinyl tetrahydrofuran

Stannane 6a underwent facile transmetalation in tetrahydrofuran at — 78 °C on treatment with butyllithium to afford 6b. Addition of the lithium reagent 6b to a solution of 1.1 equivalents of copper(I) bromide-dimethyl sulfide in 1 1 diisopropyl sulfide/tetrahydrofuran at — 78 °C gave the copper reagent 6c, which reacted with methyl vinyl ketone at —78 "C in the presence of boron trifluoride-diethyl ether65, producing 7 in 55% yield65. 

Cis- and trans 5-[2-hydroxyisopropyl]-2-methyl-2-vinyl-tetrahydrofuran (c/s/frans-furan-linalool oxides) 171/II and rosefuran 18 ... 

C/s- and trims 5-isopropyl-2-methyl-2-vinyl-tetrahydrofuran 19I/II (cis/fra/is-anhydrofuran-linalool oxides) (80MI698, 77ZLUF98) ... 

It was found that methyl vinyl ketone could be converted into 2-trimethylsilyl-1,3-butadiene by reaction with chlorotrimethylsilane (TMSC1) in the presence of triethylamie (TEA) and lithium bromide in tetrahydrofuran solution [33]. 

Methyl tetrahydrofuran Methyl vinyl ether 2-Penten-4-yn-3-ol a-Pentylcinnamaldehyde... 

Harada and coworkers went on to investigate the pseudorotaxane formation behavior of cyclodextrins with various kinds of organic polymers such as poly(methyl vinyl ether), poly(tetrahydrofuran), oligoethylene, and polyesters [94-107]. Wenz et al. reported inclusion complexation behavior between cyclodextrins and some organic polymers [108-110]. 

A screening experiment with different types of electrophilic additives showed that a promising procedure for future development was to treat methyl vinyl ketone (MVK) with chlorotrimethylsilane (TMSCl) in the presence of triethylamine (TEA) and lithium bromide in tetrahydrofuran. 

The synthesis of 2-trimethylsilyoxy-l,3-butadiene by treatment of methyl vinyl ketone with chlorotrimethylsilane, lithium bromide and triethylamine in tetrahydrofuran was discussed in section 12.5.6. It was discussed how the stoichiometry of the reaction was determined by canonical analysis of the response surface model, and how this analysis made it possible to establish experimental conditions which afforded a quantitative conversion. However, before the response surface model could be established it was necessary to find a reaction system worth optimizing. 

Procedure A. A solution of 100 mmoles of I -octene in 30 ml. of tetrahydrofurane was flushed with nitrogen and 33.3 ml. of a 1 M solution of borane in tetrahydrofurane was injected by hypodermic syringe to effect hydroboration. After 1 hr., 50 mmoles of methyl vinyl ketone in 15 ml. of tetrahydrofurane was added. After 2 hrs. at 40°, 15 ml. of water was added and the solution was heated at 40° for 1 hr. The solution was dried over magnesium sulfate for GLPC analysis ... 

Muscarine 5, one of the active ingredients in the toadstool fly agaric Amanita muscaria), contains a 2,3,5-trisubstituted tetrahydrofuran structure. A number of stereocontrolled syntheses have been worked out for muscarine. One of these starts with methyl vinyl ketone [16] and cyclizes stereoselec-tively the appropriately substituted <5-unsaturated 2,6-dichlorobenzyl ether 3 with iodine ... 

Following the previously reported synthesis of racemic muscarine from methyl vinyl ketone (28), Amouroux et al. (29) prepared both l-(+)-muscarine and its enantiomer in eight steps from d- and L-threonine, respectively, via the highly stereoselective iodocyclization of a y,8-unsat-urated 2,4-dichlorobenzylether, each being carried out separately (Scheme 4). A similar approach to tetrahydrofuran ring closure in the... 

The problem is apparently due to some residual aluminum that is hard to remove. If, however, the reduction is carried out in a iV-methylmorpholine solution, followed by addition of potassium tartrate, a pure product can be isolated. A -Methylmorpholine is a good solvent for reductions of various macromolecules with metal hydrides.In addition, the solvent permits the use of strong NaOH solutions to hydrolyze the addition complexes that form. Other polymers that can be reduced in it are those bearing nitrile, amide, imide, lactam, and oxime pendant groups. Reduction of polymethacrylonitrile, however, yields a product with only 70% of primary amine groups. Complete reductions of pendant carbonyl groups with LiAlH4 in solvents other than A -methyl-morpholine, however, were reported. Thus, a copolymer of methyl vinyl ketone with styrene was fully reduced in tetrahydrofuran. ... 

Methyl vinyl ether/maleic anhydride copolymer. See PVM/MA copolymer 2-Methyl-2-vinyl-5-(a-hydroxyisopropyl) tetrahydrofuran 2-Methyl-2-vinyl-5-(2-hydroxy-2-propyl) tetrahydrofuran. See Linalool oxide Methyl vinyl ketone... 

ATRP, atom transfer radical polymerization PIB, polyisobutylene PSt, polystyrene PMMA, poly(methyl methacrylate) POOP, polydioxapane PMVE, poly(methyl vinyl ether) PfBA, poly(/-hutyl acrylate) PAA, poly(acrylic acid) PTHF, poly(tetrahydrofuran) PTMO, poly(trimethylene oxide) MMT, montmorillonite. 

Complete reductions of pendant carbonyl groups with LiAlH4 in solvents other than N-methylmorpholine, however, were reported. Thus, a copolymer of methyl vinyl ketone with styrene was fully reduced in tetrahydrofuran [242]. 

Startg. m. allowed to react 4 hrs. with methyl vinyl sulfoxide in tetrahydrofuran in the presence of Li-diisopropylamide at -20° to room temp. product. Y 82%. K. Seki et al., Tetrah. Let. 1975, 723. 

The petroleum industry seldom encounters azeotropes because the hydrocarbon components have similar molecular stmctures. The chemical industry, on the other hand, frequently deals with components of different types, which often produce azeotropes. Common examples are the production of methyl acetate, tetrahydrofuran, tert-amyl methyl ether, isopropanol, vinyl acetate, and many others. 

Heptanal diphenyl thioacetal treated at -40 to -30 under argon with n-butyl-lithium in tetrahydrofuran during 1 hr., 0.5 equivalent Cul added at once at -78°, stirred 1 hr., a soln. of methyl vinyl ketone in tetrahydrofuran added dropwise, and stirred 2 hrs. at -78° -> y-ketothioketal (Y 80%) treated with 2 equivalents CuClg and 4 equivalents CuO in aq. 99%-acetone -> undecane-2,5-dione (Y 90%). F. y-diketones from y-ketomercaptals s. T. Mukaiyama, K. Narasaka, and M. Furusato, Am. Soc. 94, 8641 (1972). 

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