ON THE REACTION OF DIMETHYL HYDROGEN PHOSPHITE
CH3
1979
O
CH3
CH3(CH2)nCH CH2P(OMe)2
O
CH3 (CH2)n C=CH2
Ia, n = 12, 14.
IIIa
(MeO)2PH
O
II
CH3 (CH2)n CH=CH2
Ib, n = 13, 14.
CH3(CH2)nCH2CH2P(OMe)2
PhC(O)OO(O)CPh
IIIb
O
O
CH3(CH2)kCH=CH(CH2)mCH3
(MeO)2P
P(OMe)2
CH3(CH2)kCH2 CH
(CH2)mCH3
IIIc
Ic
+
CH CH2(CH2)mCH3
CH3(CH2)k
IIId
135 C with stirring and then diluted with 10 ml of
Et2O and washed with water (3 10 ml). The organic
layer was separated, dried over CaCl2, and evaporated
at 40 C first for 1h in a vacuum of 0.5 mm Hg and
then for 1 h in a vacuum of 0.06 mm Hg. The residue
was subjected to molecular film distillation at 100
110 C (0.02 mm Hg). The high-boiling fraction con-
tained phosphonates IIIa IIId, 16.7 g (81%), which
were further purified by vacuum distillation, bp 110
115 C (0.05 mm Hg), n2D0 1.4659, d420 0.9945, mp
ACKNOWLEDGMENTS
The work was financially supported by the Academy
of Sciences of the Tatarstan Republic [State Contract
no. 07-7.2-8/2006(G)].
REFERENCES
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1
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15 20 C. IR spectrum, , cm : 2940 sh, 2925 s,
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1
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3
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[3H, CH3C(H)P in IIIa]; 1.62 m (2H, PCH2CH2CH2);
1.74 m (2H, PCH2CH2); 1.96 m (1H, PCHR2 in IIIc,
IIId]; 2.04 m (2H, PCH2 in IIIa, IIIb]; 3.64 m
[(CH3O)2PCHR2 in IIIc, IIId]; 3.73 and 3.74, two d
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8.55. M 334.4 and 362.4.
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3
3
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1
spectra were taken on an Avance-600 instrument
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ternal 85% H3PO4. The EI mass spectra were regis-
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 77 No. 11 2007