CARBAMOYL AND THIOCARBAMOYL DERIVATIVES OF N-BENZYL-AMINOMETHYL-DIMETHYL-PHOSPHINE OXIDE

Abstract

A series of thirteen new carbamoyl and thiocarbamoyl derivatives of N-benzyl-aminomethyl-dimethyl-phosphine oxide have been synthesized and characterized. The compounds were prepared via interaction of N-benzyl-aminomethyl-dimethyl-phosphine oxide with the corresponding isocyanates or isothiocyanates. The composition of the synthesized novel compounds was proved by elemental analysis for nitrogen and the structures were confirmed by IR,¹H-, ³¹P-³¹P{¹H} NMR spectroscopy and by mass spectrometry.

Keywords:

• N-Benzyl-aminomethyl-dimethyl-phosphine oxide
• N-substituted-carbamoyl-(or thiocarbamoyl-)-N-benzyl-aminomethyl-dimethyl-phosphine oxides
• phosphorus-containing ureas and thioureas
• tertiary phosphine oxides

The paper is dedicated to the memory of Professor Gueorgui Borissov.

Notes

^a)The bands of CH₂ groups in the cyclohexane ring: comp. No 5at 883 (m), 2850 (m), 2933 (s); No 12 at 877 (s), 2859 (m), 2924 (s) cm⁻¹.

^b)Bands for monosubstituted Ar-ring: comp. No 8 at 742 (s) cm⁻¹ and No 9 at 735 (s) cm⁻¹.

^a Abrevations: bs, broad singlet; d, doublet; m, multiplet; s, singlet; t, triplet.

^b The signal for cyclohexane CH₂ protons of the compound were as five multiplets at 0.94–1.85 ppm. The signal for cyclohexane CH proton was a multiplet at 3.45–3.57 ppm.

^c The signal for CH₃─Ar protons was at 2.25 (s) ppm.

^d The signal for CH₃O─Ar protons was at 3.72 (s) ppm.

^e The signal for methylene Ar─CH₂─N─C(S) was at 4.75 (d) and ³ J _HH = 5.06 Hz, because of the coupling with NH─C(S) thioamide proton. After deuterium exchange with CD₃OD it changes to a singlet.

^f The signals for cyclohexane CH₂ protons were as five multiplets at 0.99–1.99 ppm. The signal for cyclohexane CH proton was a multiplet at 4.13–4.20 ppm and overlapped with the resonance signal for CH₂P(O) protons.

^g The resonace signal for ethyl CH₃ protons was at 1.08 (t) ppm with ³ J _HH = 7.25 Hz. The resonance signal for ethyl CH₂ protons was a multiplet at 3.53–3.58 ppm.

^h The resonance signals for butyl protons were respectively at: CH₃-C─C─C─NH─C(S) at 0,80 (t) ppm with ³ J _HH = 7.55 Hz, C─CH₂─C─C─N─C(S) at 1.19 (m) ppm, C─C─CH₂C─N─C(S) at 1.43–1.47 (m) ppm and the signal overlapped with the resonance signal for (CH₃)₃P(O) protons and for C─C─C─CH₂N─C(S) at 3.49–3.55 (m) ppm.