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The structure of α-(1,2-dithiole-3-ylidene) ketones and α-(1,2-dithiole-3-ylidene) aldehydes studied by means of n.m.r. spectroscopy

✍ Scribed by Carl Th. Pedersen; Erik G. Frandsen; Kjeld Schaumburg


Publisher
John Wiley and Sons
Year
1977
Tongue
English
Weight
615 KB
Volume
9
Category
Article
ISSN
0749-1581

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✦ Synopsis


Abstract

1H and ^13^C n.m.r. studies of a series of twelve 1,2‐dithiole‐3‐ylidene ketones and aldehydes have shown that the geometry of the carbon backbone is the same as found in 1,6,6aλ^4^‐trithiapentalenes. No evidence has been found which favours a bicyclic structure for the system. A linear correlation of observed ^13^C chemical shifts with calculated charge densities is found to be valid. The observations are in agreement with a structure which is a hybrid between a true ketonic structure and a true mesoionic structure.

By using the difference in the ^13^C chemical shifts of ortho and meta carbon atoms in substituent phenyl groups it is possible to qualify the degree of coplanarity of the phenyl groups with the backbone of the molecule.


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