The Journal of Organic Chemistry

Desilylative nitration of alkyl-and allylsilanes with nitronium salts

GA Olah, C Rochin

Index: Olah, George A.; Rochin, Christophe Journal of Organic Chemistry, 1987 , vol. 52, # 4 p. 701 - 702

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Citation Number: 36

Abstract

Summary: Desilylative nitration of methyl-and ethylsilanes with nitronium tetrafluoroborate in sulfolane solution gives nitromethane and nitroethane, respectively. Higher alkylsilanes are also nitrated, but the reactions are followed by HN02 elimination. The method represents the first successful nitrodesilylations at saturated carbon. Allylsilanes react cleanly with NOzBF4 in methylene chloride solution to give nitropropenes in good to excellent yield. These ...