7-(tert-Butyl­diphenyl­sil­yloxy)-2,2-dimethyl-1-benzofuran-3(2H)-one

Salas, C.O.; Tapia, R.A.; Macías, A.

doi:10.1107/S1600536810054462

Volume 67
Part 2
Page o375
February 2011

Received 15 December 2010
Accepted 27 December 2010
Online 12 January 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.111
Data-to-parameter ratio = 15.2
Details

7-(tert-Butyldiphenylsilyloxy)-2,2-dimethyl-1-benzofuran-3(2H)-one

Cristian O. Salas,^a ^* Ricardo A. Tapia ^a and Alejandro Macías ^b

^aDepartamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, 702843 Santiago de Chile, Chile, and ^bDepartamento de Química Inorgánica, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Correspondence e-mail: cosalas@puc.cl

The title compound, C₂₆H₂₈O₃Si, is an allylic oxidation product of the tert-butyl(2,2-dimethyl-2,3-dihydrobenzofuran-7-yloxy)diphenylsilane with N-bromosuccinimide and 2,2'-azobis-isobutyronitrile. The nine-atom bicyclic system is almost planar, with an r.m.s deviation of 0.0123 (2) Å and a maximum deviation of 0.031 (2) Å for the O atom. In the crystal, the molecules pile up along the b axis but the strongest intermolecular contacts are the [pi] - [pi] stacking interactions between the benzene rings along the c axis [centroid-centroid distance = 3.655 (3) Å].

Related literature

Benzofuranones are precursors of a wide range of natural and synthetic products. For a related transformation of benzofuranones in aurones, see: Schoepfer et al. (2002); Löser et al. (2004); in spiroannulated and aromatic spiroketal compounds, see: Braun et al. (2008); Zhou et al. (2008); in benzofurane derivatives, see: Venkatesan et al.(2010); and in pyranobenzofuranes, see: Foroumadi et al. (2009).

Experimental

Crystal data

C₂₆H₂₈O₃Si
M_r = 416.57
Triclinic, $[P \overline 1]$
a = 9.8210 (18) Å
b = 11.081 (2) Å
c = 12.025 (2) Å
= 98.803 (2)°
= 112.151 (2)°
= 101.791 (2)°
V = 1147.7 (4) Å³
Z = 2
Mo K radiation
= 0.13 mm^-1
T = 100 K
0.49 × 0.43 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.941, T_max = 0.988
14369 measured reflections
4197 independent reflections
3325 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.111
S = 1.05
4197 reflections
276 parameters
H-atom parameters constrained
_max = 0.83 e Å^-3
_min = -0.29 e Å^-3

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2320 ).

Acknowledgements

We gratefully acknowledge the Unidade de Raios X, RIAIDT, University of Santiago de Compostela, Spain.

References

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organic compounds