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, NaNO 2 (10 equiv), Ce(NH 4 ) 2 (NO 3 ) 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.