SYNTHESIS AND MASS SPECTRA OF FIVE-MEMBERED HETEROCYCLES CONTAINING PHOSPHORUS, OXYGEN, AND SULFUR

Abstract

Isopropylphosphonic and isopropylphosphonothioic dichlorides were esterified with ethylene glycol, mercaptoethanol, 1,2,-ethanedithiol, 2,3-buthanediol, propylene glycol, and styrene glycol, to their corresponding phosphorus-containing heterocycles, which were new tetravalent phospholanes. The structure of each heterocycle was characterized by its IR, ¹H NMR, and electron-impact mass spectrometry. The mass spectra of synthesized phospholanes were studied in detail. The molecular ions were observed in variable abundance depending on the heteroatom of the ring. The base peaks of the spectra of phospholane-2-oxides usually arise by cleavage of the P—C bond and phospholane-2-sulfides generally arise by the loss of C₃H₇S·. Plausible fragmentation pathways are described.