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Carbonyl and Thiocarbonyl Compounds: Reactions of 4-Chloroxanthione with Diazoalkanes and Compounds containing Active Hydrogen

✍ Scribed by Zeid, Ibrahim ;Yassin, Salah ;El-Sakka, Ibrahim ;Abass, Atif

Publisher
John Wiley and Sons
Year
1984
Tongue
English
Weight
256 KB
Volume
1984
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

While 4‐chloroxanthione 1 gives with diazomethane the dithiol 2, it reacts with other diazoalkanes to give the episulfides 3–5, desulfurization of which forms the ethylenes 6 and 7. Malononitrile and ethyl cyanoacetate react with 1 to give the cyano derivatives 8a, b. With hydrazines and p‐toluidine, 4‐chloroxanthione (1) give the hydrazones 9a, b and the Schiff's base 9c, respectively. The hydrazone 9a on oxidation may give either the corresponding diazo compound 10 or the ketazine 11 according to the reaction conditions. The title compound 1 reacts with hydroxylamine to yield the oxime 9d which forms the N‐phenylcarbamate 9e when treated with phenyl isocyanate.

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