The Preparation and Properties of Some Vinyl and Glycidyl Fluoroethers

Brey, Mary Louise; Tarrant, Paul

doi:10.1021/ja01581a048

Cited by 32 publications

(13 citation statements)

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“…This is due to rotational isomerism about the C-O bond, and the two bands accordingly show variations in their relative intensities with temperature. In the special case of the compound [25] CH 2 =CHoO°CH 2°C HFCI rotation is apparently inhibited by the CFCI group, and only a single band is shown. In other instances three bands appear.…”

Section: The Effects Of Attachment Of Elements Other Than Carbon (A~ mentioning

confidence: 93%

“…A substantial number of vinyl ethers have been examined by various workers [25][26][27][28][29], and detailed analyses of the individual spectra have been attempted [27][28][29]. There is general agreement that the C=C absorption appears as a doublet with band centres near 1612 cm-I and 1635 cm-I .…”

Section: The Effects Of Attachment Of Elements Other Than Carbon (A~ mentioning

confidence: 99%

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Alkenes and Vibrations of C=N and N=N Links

Bellamy¹

1980

The Infrared Spectra of Complex Molecules

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A good deal of new data has accumulated on the positions of C=C absorptions in different chemical environments, so that we are now in a better position to discuss the various factors which control the frequency shifts. But it is clear that, in this instance, both chemical and physical factors are important, and much remains to be done to determine the relative impacts of each. These two factors can be simply defined as follows. Chemical effects arise from alterations in the electron distribution within the bond which follow the replacement of one substituent by another. There is therefore a change in bond character which is reflected in an altered force constant and a shift in the vibrational frequency. However, the vibrational frequency can also be affected by factors such as substituent mass, bond-angle changes and vibrational coupling. These are purely physical effects, and they do not correspond to any change in the force constant of the bond, except insofar as angle changes may affect the hybridization. In many situations both types of effect are in operation. In conjugated systems, for example, the force constant of the bond is lowered as compared with the non-conjugated case, due to the delocalization of the 7t electrons. This leads to a shift to lower frequencit:s. However, there is now an increased possibility of vibrational coupling between the two C=C links, which will modify the frequency, although in itself it does not alter the force constants.Some of the most informative studies in this field have been those concerned with the effects of bond-angle changes and of ring strain, and these will therefore be considered first, as they illustrate very well the substantial impact of physical effects, and the difficulties which arise in disentangling them from the chemical effects which occur simultaneously.

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Section: The Effects Of Attachment Of Elements Other Than Carbon (A~ mentioning

confidence: 93%

Section: The Effects Of Attachment Of Elements Other Than Carbon (A~ mentioning

confidence: 99%

Alkenes and Vibrations of C=N and N=N Links

Bellamy¹

1980

The Infrared Spectra of Complex Molecules

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“…The structures of these molecules are also interesting because of the possibility of pi interactions involving the unshared electrons on the oxygen and the double bond in the vinyl group. In corresponding hydrogen-containing molecules, electron delocalization requires that the two olefinic carbons and the four atoms attached to them all be in the same plane [3] and leads to the existence of two isomers [4] as shown for a simple case in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

19F and 13C spectra of fluorinated and partially fluorinated vinyl alkyl ethers

Brey

2005

Journal of Fluorine Chemistry

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“…1-3,7-10 The use of a basic medium in the last two ways initiates side processes such as oligomerization and hydrolysis, thus substantially lowering the yields of the target compounds. 2,8, 9 Here we proposed an alternative route to fluorine containing glycidyl ethers starting from allyl glycidyl ether 1 and polyfluoroalkyl iodides (R F I) 2a-d.…”

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confidence: 99%