THE REACTION OF ALKYL PHOSPHITES WITH α,ß-UNSATURATED NITRILES, ANILS AND OXIMES DERIVED FROM AROMATIC ALDEHYDES

Abstract

Reactions of dialkyl phosphites (DAP, 1a, b) and trialkyl phosphites (TAP, 2a, b) with the α,β-unsaturated nitriles (3a, b and 4a, b) as well as with anils (5a and 6) derived from aromatic aldehydes (vanillin and/or piperonal) are reported. Structures of the new phosphonate products (cf. 7,8,15,16 and 17) were based upon compatible elementary and spectroscopic results Tervalent phosphites (TAP, 2a, b) and triphenylphosphine convert vanillin-oxme (5b) into 4-hydroxy -3-methoxybenzonitrile (19). Possible reaction mechanisms to account for formation of compounds 7a-d, 8a, b and 19 were also postulated.

Key Words:

• Alkyl phosphates
• vanillin, piperonal
• α,β-unsaturated nitriles
• imines
• oximes