[1885-79-6]  · C9H12NOP  · 3-Methyl-2-phenyl-1,3,2-oxazaphospholidine  · (MW 181.19)

(formation of thiophosphoramides1)

Physical Data: bp 75-78 °C/0.05 mmHg.

Solubility: sol chloroform.

Form Supplied in: clear liquid; becomes viscous on standing.

Analysis of Reagent Purity: bp and 31P NMR (143.1 ppm).

Preparative Method: prepared by heating a mixture of phenylphosphorus dichloride and N-methylethanolamine at 130 °C (81%).2

Purification: distillation in vacuo immediately before use.

Handling, Storage, and Precautions: hygroscopic. Dimerizes and polymerizes on standing.

General Discussion.

The title compound (1) undergoes dimerization (eq 1) at rt to form a ten-membered macrocycle. This compound has been isolated as a mixture of two isomers.3

Treatment of (1) with Diphenyl Disulfide results in production of (2), presumably by alkylation on phosphorus followed by ring opening by the phenylthiolate anion (eq 2).1

1. Bentrude, W. G.; Kawashima, T.; Keys, B. A.; Garroussian, M.; Heide, W.; Wedegaertner, D. A. JACS 1987, 109, 1227.
2. Mukaiyama, T.; Yokota, Y. BCJ 1965, 38, 858.
3. Dutasta, J. P.; Martin, J.; Robert, J. B. H 1980, 14, 1631.

Mark S. Meier

University of Kentucky, Lexington, KY, USA

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