Abstract
The carbanion [(RO) 2P(O)][C(O)NEt 2]CH − is used to prepare several new carbamoylmethyl phosphonates of the general type [(RO) 2P(O)][C(O)NEt 2]CH(X), XCH 3, C 2H 5, (CH 2) 2CN, CH 2CH[(RO) 2P(O)][C(O)NEt 2], (CH 2) 3OH and CH 2C(O)OCH 3. In addition, an interesting intramolecular transesterification process for the molecule with X(CH 2) 3OH and novel hydrolysis chemistry that produces useful phosphonic acids are described. The molecular structure determinations of two compounds, {[(i-PrO) 2P(O)][C(O)NEt 2]CH} 2CH 2 ( 4b) and [ NH 2C(CH 3) 2CH 2C(O)CH 2C(C H 3) 2 +][(HO)PO 2CH 2C(O)NEt 2 −] (bd11) are outlined. Compound (bd4b) crystallizes in the triclinic space group P1, with a=9.0996(24), b=12.6604(31), c=16.5711(48) Å, α=68.655(20), β=78.714(22), γ=70.742(19)° and Z=2. The molecular structure confirms that two carbamoylmethyl phosphonate fragments are bonded to a central methyl group. Compound 11 crystallizes in the triclinic space group P1, with a=9.2384(21), b=9.8404(21), c=11.0702(25) Å, α=85.276(18), β=74.477(17), γ=78.644(17)° and Z=2. The molecular structure contains a 2,2,6,6-tetramethyl piperidone cation and a carbamoylmethyl phosphonic acid anion.
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