240
Boyd, Buksha, Coumbarides, Dingjan, Eames, Jones, Motevalli, Stenson, and Suggate
µ = 0.085 mm−1, F(0 0 0) = 448. There were
1903 independent reflections [Rint = 0.0099]. The
final R indices were [I > 2σ(I)] R1 = 0.0460,
3. Cuenca, A.; Medio-Simon, M.; Aguilar, G.A.; Weibel, D.;
Beck, A.K.; Seebach, D. Helv. Chim. Acta. 2000, 83, 3153.
4a. Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymme-
try 1997, 8, 3293
4b. Fuji, K.; Tanaka, K.; Miyamoto, H. Tetrahedron: Asymmetry
1993, 4, 247.
wR2 = 0.0975
(all
data)
R1 = 0.1290,
wR2 = 0.1202. The largest difference peak
5. This is due to their reduced basicity as a consequence of com-
petitive conjugation of the enol oxygen onto the neighboring
=
−3
˚
and hole was 0.180 and − 0.211 e A .
C
O group.
6a. Coumbarides, G.S.; Eames, J.; Weerasooriya, N. Eur. J. Org.
Chem. 2002, 181
6b. Coumbarides, G.S.; Eames, J.; Weerasooriya, N. J. Label
Compd. Radiopharm. 2001, 44, 871
4-Phenyl cyclohexenyl acetate 9
6c. Coumbarides, G.S.; Eames, J.; Weerasooriya, N. Bull. Chem.
Soc. Jpn. 2002, 75, 1163.
7a. Fehr, C. Angew. Chem. Int. Engl. 1996, 35, 2566, and refer-
ences therein;
C14H16O2, Mr 216.27, triclinic, space
˚
˚
group P-1, a = 7.146(4) A, b = 9.018(6) A,
◦
◦
7b. Duhamel, L.; Duhamel, P.; Plaquevent, J.C. Tetrahedron:
˚
c = 9.560(8) A, α = 92.38(8) , β = 71.77(7) ,
Asymmetry 2004, 15, 3653.
8a. Asensio, G.; Aleman, P.A.; Cuenca, A.; Gil, J.; Medio-Simo´n,
M. Tetrahedron: Asymmetry 1998, 9, 4073
8b. Asensio, G.; Aleman, P.A.; Cuenca, A.; Gil, J.; Domingo, L.R.;
Medio-Simo´n, M. J. Org. Chem. 1998, 63, 9342
8c. Asensio, G.; Gavina, P.; Cuenca, A.; de Arellano, M.C.R.;
Domingo, L.R.; Medio-Simo´n, M. Tetrahedron: Asymmetry
2000, 11, 3481
8d. Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60,
1914.
9. Coumbarides, G.S.; Boyd, E.; Eames, J.; Hay, A.; Stenson,
R.; Suggate, M.J.; Jones, R.V.H. Tetrahedron Lett. 2004, 45,
9465.
γ = 87.27(10)◦, V = 580.0(7) A , Z = 2,
3
˚
Dca = 1.238 Mg m−3, µ = 0.081 mm−1,
F(0 0 0) = 232. There were 2035 independent re-
flections [Rint = 0.0098]. The final R indices were
[I > 2σ(I)] R1 = 0.0497, wR2 = 0.1264 (all data)
R1 = 0.0851, wR2 = 0.1430. The largest differ-
−3
˚
ence peak and hole was 0.315 and − 0.258 e A .
10a. Heeg, M.J. Acta Crystallogr., Sect. C, Struct. Crystallogr.
Acknowledgments
Commun. 1987, 43, 2017
10b. Olesen, B.; Bond, M.R. Acta Crystallogr., Sect. C, Struct.
Crystallogr. Commun. 2004, 60, o196
We are grateful to the Royal Society, the
University of London Central Research Fund and
Syngenta (Grangemouth, Scotland) for their fi-
nancial support, the EPSRC National Mass Spec-
trometry Service (at Swansea, UK) for accurate
mass determinations, and the EPSRC National
Crystallographic Service (at Southampton, UK)
for data collection on compound 5.
10c. Jimenez-Vazquez, H.A.; Ochoa, M.E.; Zepeda, G.; Modelli,
A.; Jones, D.; Mendoza, J.A.; Tamariz, J. J. Phys. Chem. A
1997, 101, 10082
10d. Cantrell, T.S.; Silverton, J.V. J. Org. Chem. 1979, 44, 4477
10e. Zhdanov, Y.A.; Olekhnovitch, L.P.; Simakov, V.I.; Furmanova,
N.G.; Minkin, V.I. Dokl. Akad. Nauk. SSSR (Russ.) (Proc. Nat.
Acad. Sci. USSR) 1985, 282, 1389
10f. Wadsworth, D.H.; Bender, S.L.; Smith, D.L.; Luss, H.R.;
Weidner, C.H. J. Org. Chem. 1986, 51, 4639
10g. Hashmi, A.S.K.; Bats, J.W.; Choi, J.-H.; Schwarz, L. Tetrahe-
dron Lett. 1998, 39, 7491
10h. Langer, P.; Eckardt, T.; Schneider, T.; Gobel, C.; Herbst-Irmer,
R. J. Org. Chem. 2001, 66, 2222
10i. Golobic, A.; Koller, J. J. Mol. Struct. 2001, 532, 109
10j. Ruberu, S.R.; Fox, M.A. J. Am. Chem. Soc. 1992, 114, 6310
10k. Bartels-Rahm, B.; Field, J.S.; Emslie, N.D. Tetrahedron 1998,
54, 3255
10l. Robinson, P.D.; Lutfi, H.G.; Hou, Y.; Meyers, C.Y. Acta Crys-
tallogr., Sect. C, Struct. Crystallogr. Commun. 2001, 57, 428
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