Organic Phosphorus Compounds 60. The direct synthesis of tris(N‐substituted carbamoylethyl) phosphine oxides

Abstract

The reaction of elemental white phosphorus with N‐alkyl acrylamides and N,N‐dialkyl acrylamides in the presence of a base is described and the physical properties of 8 new tertiary phosphine oxides of general formula (R2NCOCH2CH2)3PO (R = H, CH3, C2H5,(CH2)4, (CH2)5, and C2H4OC2H4, CH2CHCH2) are reported. Interaction of white phosphorus with RNCS, RNCO, azo‐bis‐isobutyronitrile, Ph2NNPh2, vinyl acetate, vinyl ethyl ether, and expoxides has also been investigated.

Unusual Regioselectivity of the Dipolar Cycloaddition Reactions of Nitrile Oxides and Tertiary Cinnamides and Crotonamides1

“…After being stirred at room temperature for 2 h, the reaction mixture was poured into 1 N HCl (50 mL) and extracted. Found: C,74.49;H,10.97;N,6.62. N,N-Diethylacrylamide (17b): oil, ref 27. If necessary, the amides were purified by recrystallization or column chromatography generally using ethyl acetate/hexanes.…”