STUDIES ON ORGANOPHOSPHORUS COMPOUNDS 67. REACTIONS OF α-NITROALKENES WITH COMPOUNDS BEARING ACTIVE METHYLENE GROUPS. A NOVEL AND CONVENIENT SYNTHESIS OF 2-ISOXAZOLINE DERIVATIVES

Abstract

Reaction of α-nitroalkenes and compounds bearing an active methylene group followed by subsequent addition of trimethylchlorosilane leads to a series of 2-isoxazoline derivatives in good yield. The reaction proceeded through the formations of an alkene and a silyl nitronate as a 1,3-dipole. The reaction mechanisms and the chemical behaviour of the products are discussed.

Key Words:

• Silyl nitronate
• silyl migration
• 1,3-dipole