Ethyl allyl ether

Peroxides. These are formed by aerial oxidation or by autoxidation of a wide range of organic compounds, including diethyl ether, allyl ethyl ether, allyl phenyl ether, dibenzyl ether, benzyl butyl ether, n-butyl ether, iso-butyl ether, r-butyl ether, dioxane, tetrahydrofuran, olefins, and aromatic and saturated aliphatic hydrocarbons. They accumulate during distillation and can detonate violently on evaporation or distillation when their concentration becomes high. If peroxides are likely to be present materials should be tested for peroxides before distillation (for tests see entry under "Ethers", in Chapter 2). Also, distillation should be discontinued when at least one quarter of the residue is left in the distilling flask. 

Individually indexed compounds include f Allyl ethyl ether, 1955... 

The slow carbozincation, attributed to the presence of TMEDA, was more problematic when substrate-induced diastereoselection was also involved. Thus, addition of zincated allyl ethyl ether to the alkenyllithium derived from the secondary y-iodo allylic ether 209 afforded a 65/35 mixture of the diastereomers 228 and 229 in low yield after hydrolysis. The erosion of diastereoselectivity was not a consequence of a less efficient substrate-induced diastereoselection but rather of the fact that both the (E) and (Z) isomers of the zincated allyl ethyl ether had reacted. Although the use of a catalytic amount of TMEDA (10 mol%) in the metallation step substantially improved the yield, the diastereoselectivity remained low (equation 111)151. 

Nevertheless, chiral propargylic amines remain interesting substrates for achieving the diastereoselective addition of substituted allylic organozinc compounds to metallated alkynes. Besides crotylzincation, one example of diastereoselective addition of zincated allyl ethyl ether to 328 has also been reported183. 

In the same study, maleimides were irradiated in the presence of allyl alcohol and allyl ethyl ether, yielding the respective cyclobutanes with significant exo-preference [115]. Diastereofadal stereocontrol was achieved in the [2 + 2]-photo-cycloaddition of tetrahydrophthalimide by a chiral tether. The valinol-derived sub-... 

Rnally, mercuryfll) oxide in combination with fluoroboric acid and ethanol in THF solution has been shown to convert aUylbenzenes into the rearranged allylic ethyl ethers. ... 

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