Tetrahedron p. 3919 - 3928 (1998)
Update date:2022-08-03
Topics:
Bryce, Martin R.
Chalton, Michael A.
Chesney, Antony
Catterick, David
Yao, Jing W.
Howard, Judith A.K.
New 1,3-dithiol-2-ylidene derivatives, notably π-extended systems, have been synthesised by Wittig reactions of phosphorane and phosphonate ester derivatives of 1,3-dithiole with activated ketones and α,β-unsaturated ketones. Nitrosation reactions of a range of these π-extended systems, results in the formation of nitroalkenes, via unstable nitrosoalkene intermediates, which, in general, could not be isolated. The X-ray crystal structure of 1-(4,5-dicarbomethoxy-1,3-dithiol-2-ylidene)-1-cyano-1-phenyl- methane reveals a small degree of intramolecular electron transfer from the dithiole ring to the conjugated cyano group.
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Doi:10.1021/je60039a038
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