M. B. Smith, M. R. J. Elsegood / Tetrahedron Letters 43 (2002) 1299–1301
1301
An X-ray structure (Fig. 1)§ of 1j confirms that the
overall geometry comprises ortho-substituted
References
1. (a) Mino, T.; Kashihara, K.; Yamashita, M. Tetrahedron:
Asymmetry 2001, 12, 287; (b) Lange, P.; Schier, A.;
Schmidbauer, H. Inorg. Chem. 1996, 35, 637.
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2000, 122, 12379.
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Stelzer, O.; Hausler, T.; Sheldrick, W. S. J. Organomet.
Chem. 2000, 598, 116.
-N(H)CH2PPh2 and -CO2H groups (in addition to the
two methoxy groups).¶ Hydrogen bonding is also evi-
dent and links molecules into head-to-tail dimer pairs
through hydrogen bonding [O(2)···O(1A) 2.646(1),
,
H(2)···O(1A) 1.81(3) A; O(2)ꢀH(2)···O(1A) 169(2)°].
There is also an intramolecular NꢀH···O hydrogen
,
bond [N(1)···O(1) 2.713(2), H(1)···O(1) 2.04(2)A;
N(1)ꢀH(1)···O(1) 137(2)°].
4. Hingst, M.; Tepper, M.; Stelzer, O. Eur. J. Inorg. Chem.
1998, 73.
In conclusion, we have developed a facile procedure for
the synthesis of new functionalised tertiary phosphines
bearing carboxylic acid groups. This synthetic route is
extremely practical with reactions generally complete
within a few hours. In addition to the short reaction
times this method obviates the preparation of reactive
intermediates, uses cheap and commercially available
starting materials, requires no purification steps nor
any stringent need for performing reactions under an
oxygen free atmosphere. Current efforts are directed
towards understanding their co-ordination behaviour
and potential utility in catalysis.
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§ Crystal data for 1j: C22H22NO4P, Mw=395.38; monoclinic, space
,
group P21/c, a=10.0587(8), b=19.0185(15), c=11.1660(9) A, i=
3
113.342(2)°; U=1961.2(3) A , Dcalcd=1.339 g cm−3, u(Mo Ka)=
,
0.71073 A, Z=4, v=0.169 mm−1, T=150(2) K, wR2=0.1153 for all
,
4698 unique data, R1=0.044 for 3473 reflections with F2>2|(F2).
The -PPh2 unit is disordered over two sets of positions; ratio of
major:minor components 84:16(1). Crystallographic data (excluding
structure factors) for the structure in this paper has been deposited
with the Cambridge Crystallographic Data Centre as supplementary
publication number CCDC 177016. Copies of the data can be
obtained, free of charge, on application to CCDC, 12 Union Road,
¶
,
Selected bond lengths (A) and angles (°): P(1)ꢀC(1) 1.8208(19),
P(1)ꢀC(11) 1.830(2), P(1)ꢀC(17) 1.838(2), C(1)ꢀN(1) 1.456(2),
N(1)ꢀC(2) 1.367(2), C(8)ꢀO(1) 1.246(2), C(8)ꢀO(2) 1.329(2).
C(1)ꢀP(1)ꢀC(11)
100.60(10),
C(1)ꢀP(1)ꢀC(17)
101.07(10),
C(11)ꢀP(1)ꢀC(17) 100.84(12), P(1)ꢀC(1)ꢀN(1) 111.56(13).