ULTRASONIC NITRATION OF ALLYLSILANES BY USE OF SODIUM-NITRITE AND CERIC AMMONIUM-NITRATE

An efficient method was developed for synthesis of a new class of comp ounds, 1-nitro-3-organosilyl-1-propenes. Sonication of a chloroform so lution 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 degrees C afforded 1-nitro-3-orga nosilyl-1-propenes in 51-86% yields. By the same method at 25-73 degre es C, various olefins, styrene, benzofuran, and indene were converted to the corresponding alpha,beta-unsaturated nitro olefins in 54-99% yi elds. Advantages associated with this new nitration method include mil d conditions, high regioselectivity, good to excellent yields, and a s hort period of reaction time.