J Chem Crystallogr (2012) 42:251–257
257
Synthesis of 4,5-Bis(diphenylphosphino)-9-
Isopropylidenexanthene (2)
Supplementary Material
Crystallographic data in cif format for the structural anal-
ysis has been deposited with the Cambridge Crystallo-
graphic Data Centre, with numbers CCDC 844482–844484
for compounds 1–3 respectively. Copies of this information
may be obtained free of charge from: The Director, CCDC,
12 Union Road, Cambridge, CB2 1EZ, UK. Fax:
?44(1223)336-033, e-mail:deposit@ccdc.
Compound 2 was prepared analogously to compound 1
using 10-isopropylidenexanthene (1.5 g, 6.8 mmol),
TMEDA (2.6 mL, 17.2 mmol), 1.6 M nBuLi (10.8 mL,
17.2 mmol) and PPh2Cl (3.2 mL, 17.2 mmol) in hexane
(7.5 mL). Recrystallization from DCM/EtOH (1:1) affor-
ded yellow crystals of 2 suitable for X-ray analysis. [yield:
2.1 g, 52%; m.p. 487 K]. Spectroscopic analysis: 1H NMR
(400 MHz, CDCl3, d, ppm): 7.33 (dd, J = 7.6, 1.5 Hz,
2H), 7.25–7.11 (m, 20H), 6.96 (t, J = 7.6 Hz, 2H), 6.54
(dquar, J = 7.6, 1.7, J(P,H) = 1.7 Hz, 2H), 2.07 (s, 6H);
13C NMR (101 MHz, CDCl3, d, ppm): 156.0 (t,
J(P,C) = 20 Hz, CO), 137.2 (dd, J(P,C) = 6.5, 6.0 Hz,
phenyl C-ipso, PC), 134.0 (t, J (P,C) = 21 Hz, phenyl
CH),131.5 (CH), 131.3 (C), 128.2 (CH), 128.2 (t,
J(P,C) = 6.8 Hz, phenyl CH), 126.3 (CH), 125.7 (dd,
J(P,C) = 1.9, 11 Hz, CHCHC–P), 122.8 (C), 122.7 (CH),
23.2 (CH3).; 31P NMR (243 MHz, CDCl3 d, ppm): -17.9;
IR (neat, mmax, cm-1): 3058 (m), 2931 (m), 1433 (s), 1477
(m), 1393 (s), 1221 (s), 1178 (s), 801 (m), 739 (m), 692
(m), 504 (s); HR–MS (ESI) (m/z): 591.2002. [M ? H]?
calcd. for C40H33OP2, 591.2001.
Acknowledgments We thank Dr Manuel Fernandes for X-ray data
collection. SASOL, THRIP, University of KwaZulu-Natal and the
NRF are acknowledged for financial support.
References
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Crystal Structure Determinations
The crystal data for compounds 1, 2 and 3 were collected at
low temperature (T = 173 K), using a Bruker APEX II
CCD area detector diffractometer with graphite mono-
chromated Mo Ka radiation (50 kV, 30 mA) using the
APEX 2 [16] data collection software. Data reduction was
carried out using the program SAINT? [17]. The crystal
structure was solved by direct methods using SHELXTL
[18]. All H atoms attached to C atoms were fixed geo-
˚
metrically and treated as riding with C–H = 0.95 A and
15. Marimuthu T, Bala MD, Friedrich HB (unpublished work)
16. Bruker (2005) APEX2. Version 2009.1-0. Bruker AXS Inc.,
Madison, Wisconsin, USA
17. Bruker (2005) SAINT?. Version 7.60A. (includes XPREP and
SADABS) Bruker AXS Inc., Madison, Wisconsin, USA
18. Bruker (1999) SHELXTL. Version 5.1. (includes XS, XL, XP,
XSHELL) Bruker AXS Inc., Madison, Wisconsin, USA
19. Farrugia LJ (1997) J Appl Cryst 30:565
˚
U
U
iso(H) = 1.2Ueq(C) for phenyl H and C–H = 0.95 A and
iso(H) = 1.2Ueq(C) for methyl H. The molecular structure
plots for all compounds were prepared by ORTEP-3 [19]
and OLEX2 [20]. Crystallographic data and details of the
data collection and structure refinements are listed in
Table 1. Selected bond lengths and angles for compounds
1–3 are presented in Table 2. Detailed crystallographic
information is found in the supplementary data.
20. Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Pusch-
mann H (2009) J Appl Cryst 42:339–341
123