Cyclopropyl methyl ether

Cinnamaldehyde, 3134 f Crotonaldehyde, 1516 f Cyclopropyl methyl ether, 1608 f Diallyl ether, 2431... 

Azatricyclo[2.2.1.02 6]hept-7-yl perchlorate, 2368 f Azetidine, 1255 Benzvalene, 2289 Bicyclo[2.1.0]pent-2-ene, 1856 2-/ert-Butyl-3-phenyloxaziridine, 3406 3 -Chloro-1,3 -diphenyleyclopropene, 3679 l-Chloro-2,3-di(2-thienyl)cyclopropenium perchlorate, 3388 Cyanocyclopropane, 1463 f Cyclopropane, 1197 f Cyclopropyl methyl ether, 1608 2,3 5,6-Dibenzobicyclo[3.3.0]hexane, 3633 3,5 -Dibromo-7-bromomethy lene-7,7a-dihy dro-1,1 -dimethyl-1H-azirino[l,2-a]indole, 3474 2.2 -Di-tert-butyl-3.3 -bioxaziridinc, 3359 Dicyclopropyldiazomethane, 2824 l,4-Dihydrodicyclopropa[ >, g]naphthalene, 3452 iV-Dimethylethyl-3,3-dinitroazetidine, 2848 Dinitrogen pentaoxide, Strained ring heterocycles, 4748 f 1,2-Epoxybutane, 1609 f Ethyl cyclopropanecarboxylate, 2437 2,2 -(l,2-Ethylenebis)3-phenyloxaziridine, 3707 f Methylcyclopropane, 1581 f Methyl cyclopropanecarboxylate, 1917 f Oxetane, 1222... 

Figure 10.3.1 Estimation of Tm for cyclopropyl methyl ether using the method of Joback and Reid [10].

Suppose that the compound s phase at 25°C was of interest. This question would have been answered correctly for all three compounds, although the quantitative estimation of Tm is not very precise. Suppose that the compound s phase at 20°C was of interest. This question would have been answered correctly for cyclopropyl methyl ether and 1,2-cyclopentenophenanthrene, but not for anethol. The magnitude of the interval (7 m)estimated - Timerestl can serve as a confidence measure for binary decision of the foregoing type. If (7 m)estimated interestI is lower than 50°C, a decision as to whether a compound is fluid or solid at interest should not be made based on Tm estimated using the method of Joback and Reid. 

On the other hand, cation formation by decarboxylation of an acyloxonium cation RC02+ is supported by the partial stereospecificity observed in the electrolysis of cis- and trans-bicyclo [3.1.0] hexane-3-carboxylic acid 2°5 and the electrocyclic ring opening in the anodic oxidation of 3-methyl-2-phenylcyclopro-panecarboxylate (22, 23) to cyclopropyl methyl ether (24, 25) and allylic ethers (26, 27) (Eq. (97)) 206). 

Z (CH3CH2)20—AICI3 14.4. (a) methoxyethene methyl vinyl ether (b) ethyl isopropyl ether 2-ethoxypropane (c) 2-chloroethyl methyl ether l-chloro-2-methoxyethane (d) 2-ethoxy-2,3-dimethylpen-tane (e) 1,1-dimethoxycyclopentane (f) tran.s-2-methoxycyclohexanol (g) cyclopropyl methyl ether methoxycyclopropane. 14.6. (a) dihy-dropyran (b) 2-chloro-1,4-dioxane (c) 3-isopropylpyran (d) trans-2,3-diethyloxirane or trans-3,4-epoxyhexane (e) 3-bromo-2-ethoxyfuran ... 

Cyclopropanol is significantly (a factor of 10 ) more reactive toward mercuric acetate than is phenyl cyclopropane. A cyclopropyl methyl ether is less reactive than the corresponding cyclopropanol by a factor of 10—20, and the cyclopropyl acetate is decreased in reactivity by a factor of nearly 10. These results are fully consistent with the large q value for the mercuration reaction reported by Oullette (vide supra). 

The experimentally determined conformations of both cyclopropanoP and cyclopropyl methyl ether are in the gauche form (37). This geometry would permit electron donation from an oxygen lone pair to the 4e LUMO of cyclopropane as shown in Figure 3, and it has been predicted by 4-3IG calculations that this geometry would be favored and contribute some stability to the molecule. 

When functional groups are present in the starting ketone, the reaction may become very complex due to competing side reactions associated with the functional groups. Examples include the condensation of cyclopropylidenetriphenylphosphorane with 2,2-dimethoxy-l-phenylethan-l-one (18), which results in formation of the desired alkylidenecyclopropane 19, as well as the stereoisomeric cyclopropyl methyl ethers 20. ... 

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... 

Cyclopropanemethanol Cyclopropanone Cyclopropane Cyclopropylamine Cyclopropylbenzene Cyclopropyl methyl ether Cyclopropyl methyl ketone... 

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