Oxidation of gem-chloronitroso- and vic-chloronitroso-alkanes and -cycloalkanes to respective chloronitro compounds by novel cetyltrimethylammonium hypochlorite reagent
Cetyltrimethylammonium hypochlorite (CTAHC) is prepared and used as an oxidizing agent for nitroso group to nitro group. The gem-chloronitroso and vic-chloronitroso compounds are prepared respectively from ketoximes and olefins by reacting with NOCl generated in situ from chlorotrimethylsilane (TMSC1 (l) and iso-amyl nitrite. CTAHC oxidizes gem-chloronitroso and vic-chloronitroso compounds to the corresponding chloronitro derivatives. While gem-chloronitro compounds are obtained in good yields, the vic-chloronitro derivatives are formed in moderate yields, because of the propensity of the vic-chloronitroso group to tautomerize to α-chlorooxime. The present method is simple and practical, particularly for the preparation of vic-chloronitro compounds, considering the fact that the known methods of their preparation are few and quite involved. Indian Academy of Sciences.
Mohammed, Abdulkarim H.A.,Nagendrappa, Gopalpur
experimental part
p. 433 - 441
(2012/03/26)
Generation of nitryl chloride from chlorotrimethylsilane-acetyl nitrate reaction: A one-pot preparation of gem-chloronitro compounds from oximes
While iso-amyl nitrite reacts with chlorotrimethylsilane to give NOCl, iso-amyl nitrate does not yield NO 2Cl with silicon reagent. However, acetyl nitrate reacts successfully with chlorotrimethylsilane to give nitryl chloride, which is charact
Mohammed, Abdulkarim H. A.,Nagendrappa, Gopalpur
experimental part
p. 571 - 577
(2010/12/20)
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