STUDIES ON PHOSPHONIUM YLIDES-XIV. THE BEHAVIOUR OF 5(4-PYRIDYL)-2-THIONO- 1,3, 4-OXADIAZOLE TOWARDS WITTIG REAGENTS

Abstract

Wittig reagents (la-c) react with 5-(4-pyridyl)-2-thiono-1,3,4-oxadiazole (II) yielding the new adducts (IIIa-d). Structural reasoning for compounds III was based on compatible analytical and spectral data (IR, ¹H NMR, ³¹P NMR, and MS). The mechanism that accounts for formation of adducts III is discussed.

Key Words:

• Wittig reagents (I)
• 5-(4-Pyridyl)-2-thiono-1,3,4-oxadiazole (III)
• Cyano-5-(4-pyridyl)-β-cyano-α-(triphenylphosphoranylidene)-2-propyl-1,3,4-oxadiazole (IIIa)
• Benzoyl-5-(4-pyridyl)-β-benzoyl-2-propene-1.3.4-oxadiazole (IIIb)
• Methyl-5-(4-pyridyl)-2-carboxyethylene-1,3,4-oxadiazole (IIIc)
• and 5-(4-Pyridyl)-2-propyl-1,3,4-oxadiazole (IIId).