Ultrasonic Nitration of Allylsilanes by Use of Sodium Nitrite and Ceric Ammonium Nitrate

Abstract

An efficient method was developed for synthesis of a new class of compounds, 1-nitro-3-organosilyl-1-propenes. Sonication of a chloroform solution containing allylsilanes with various organosilyl groups, NaNO2 (10 equiv), Ce(NH4)2(NO3)6 (2.0 equiv), and acetic acid (12 equiv) in a sealed tube at 600 W and 25−55 °C afforded 1-nitro-3-organosilyl-1-propenes in 51−86% yields. By the same method at 25−73 °C, various olefins, styrene, benzofuran, and indene were converted to the corresponding α,β-unsaturated nitro olefins in 54−99% yields. Advantages associated with this new nitration method include mild conditions, high regioselectivity, good to excellent yields, and a short period of reaction time.