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Three-bond carbon–fluorine coupling constants in substituted 3-fluoropropanes and 3-fluoropropanoates

✍ Scribed by Abderrahman Dahbi; Sylvain Hamman; Claude G. Béguin

Publisher
John Wiley and Sons
Year
1986
Tongue
English
Weight
717 KB
Volume
24
Category
Article
ISSN
0749-1581

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✦ Synopsis

Three-bond carbon-fluorine coupling constants of 32 substituted 3-fluoropropanes and 3-fluoropropanoates were measured. From these values and from those of other alicyclic compounds already known in the literature, it can be established that the influence of molecular parameters on 'J(FC) depends on the nature of the coupled carbon. When this carbon belongs to an alkyl group, the main molecular parameter is the dihedral angle [J(FC)g = 1.2 Hz and J(FC)' = 11.2 Hz]. When the carbon belongs to a carbethoxy group, more complex effects are observed: for one series the main parameter is the dihedral angle [J(FC)" = 0 Hz and J(FC)' = 20 Hz], and for other series the electronegativity and orientation of substituents particularly influence J(FC)g. Conversely, the diastereoisomers can be unambiguously identified from the 'J(HH), 'J(FH) and 3J(FC) values of both diastereoisomers.

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