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The title compound, endo,exo-12-oxotetra­cyclo­[6.2.1.13,6.02,7]­dodeca-9-en-anti-11-yl p-bromo­benzoate, C19H17BrO3, con­sists of norbornene with an anti-p-bromo­benzoate substituent at the methano bridge and an exo-fused norbornanone unit bonded to the ethano bridge. The spatially proximate ketone and alkene interact through space and the ketone C atom is substantially pyramidalized. Through-space ketone π-inter­action is probably responsible for the low solvolysis rate of the anti-11-chloride derivative.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011185/bk1550sup1.cif
Contains datablocks global, 1-OPBB

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011185/bk15501-OPBBsup2.hkl
Contains datablock 1-OPBB

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108270100011185/bk1550sup3.pdf
Supplementary material

CCDC reference: 153912

Computing details top

Data collection: COLLECT; cell refinement: DENZO-SMN; data reduction: DENZO-SMN; program(s) used to solve structure: SIR97; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1998) and ORTEP-3 (Farrugia, 1997).

(1-OPBB) top
Crystal data top
C19H17BrO3F(000) = 760
Mr = 373.24Dx = 1.55 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
a = 11.3936 (3) ÅCell parameters from 17290 reflections
b = 8.2659 (2) Åθ = 4.4–32.6°
c = 16.9840 (5) ŵ = 2.58 mm1
β = 90.6750 (17)°T = 148 K
V = 1599.41 (7) Å3Prism, colorless
Z = 40.3 × 0.23 × 0.2 mm
Data collection top
Nonius KappaCCD Diffractometer4073 reflections with I > 2σ(I)
Phi Scan scansRint = 0.023
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
θmax = 32.6°, θmin = 4.4°
Tmin = 0.511, Tmax = 0.626h = 1617
8643 measured reflectionsk = 1012
5678 independent reflectionsl = 2525
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0168P)2 + 1.2341P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.59 e Å3
5678 reflectionsΔρmin = 0.50 e Å3
276 parameters
Special details top

Experimental. The dimethoxy ketal of (1-(OCH3)2) was hydrolyzed in a manner similar to literature methods (Bertsch et al., 1988; Fessner et al., 1987; Gassman & Marshall, 1973), by stirring (1-(OCH3)2) in a 1:1 solution of 27%(w/w) HClO4 and THF at 298 K for 3 h. Solid NaHCO3 was then added until the mixture was no longer acidic. The mixture was extracted five times with CH2Cl2, shaking gently to avoid emulsion formation. The CH2Cl2 extracts were combined and washed once with saturated brine. The brine layer was extracted four times with CH2Cl2 and the CH2Cl2 extracts were combined. After evaporation of the solvents, and purification by column chromatography (silica, CH2Cl2 solvent), white crystalline diketone (1O) was isolated (88%): mp 358–359 K, 1H NMR (90 MHz, CDCl3) δ 1.57–1.80 (m, 4 H), 1.88 (m, 2 H), 2.56 (m, 2 H) 3.14 (m, 2 H), 6.42 (t, 2 H). IR (CDCl 3) 3020 s h, 2950 m, 2882 m, 1805 s h, 1763 s, 1746 s h, 1130 m, 915 s cm-1. # #Insert structure diagram 2 for synthesis here.# #

The C11O ketone was reduced (Cieplak, 1999; Ohwada, 1999, and references therein) selectively in preference to the C12O ketone to the anti-alcohol (1-OH) with LiAlH(O—C(CH3)3). Diketone (1 O) was dried (13 torr, over CaH2, 24 h). To a stirred 4.2%(w/w) solution of LiAlH4 in dry THF were slowly added 3 moles of t-butanol at 273 K. After stirring for 10 min, a cooled (273 K) 14%(w/w) solution of diketone (1O) in THF was added over 5 min at 273 K under N2. The LiAlH(O—C(CH3)3) was in a 20% molar excess. Stirring was continued as the mixture was allowed to slowly warm up to 298 K. A basic workup was then used (Fieser & Feiser, 1967). The aluminium salts were removed by vacuum filtration, and the THF solution was concentrated in vacuo. The product was purified by column chromatography (Florisil, THF solvent), yielding initially a colorless oil that crystallized on standing (1-OH) (92%): mp 351–353 K, 1H NMR (300 MHz, acetone-d6) δ 1.48–1.60 (m, 2 H), 1.62–1.66 (m, 2 H), 1.70 (m, 2 H), 2.46 (m, 2 H), 2.71 (m, 2 H), 3.56 (m, 1 H), 4.53 (m, 1 H), 5.82 (t, 2 H). 13C NMR (75 MHz, proton decoupled, acetone-d6) δ 23.06, 41.59, 43.14, 50.66, 84.59, 135.62, 215.26. IR (CDCl3), 3700–3100 s, 3060 w, 2975 s, 2876 m, 1760 s, 1733 s, 1240 m, 1085 s, 910 m cm-1.

Alcohol (1-OH) was esterified by reaction with an equimolar amount of p-bromobenzoyl chloride in a 2.05: 1 molar excess of pyridine with CH2Cl2 solvent. All materials were dry, and the mixture was warmed to reflux for 20 min. The reaction mixture was poured into cold 5% HCl, and extracted with CH2Cl2. The CH2Cl2 extracts were washed twice more with 5% HCl, and then with saturated brine. The CH2Cl2 layer was dried (MgSO4), filtered, and CH2Cl2 was evaporated. Column chromatography (Florisil, ether solvent), yielded white crystals (83%). Purity was further improved by recrystallizing three times from CH2Cl2 / ether, yielding colorless prisms: mp 448–449 K, 1H NMR (90 MHz, CDCl3) δ 1.36–1.80 (m, 4 H), 1.86 (m, 2 H), 2.44 (m, 2 H), 3.13 (m, 2 H), 4.61 (m, 1 H), 6.03 (t, 2 H), 7.59 (d, 2 H), 7.88 (m, 2 H).

Alcohol (1-OH) was converted to the chloride (1-Cl) by reaction with triphenylphosphine in carbon tetrachloride (Ashby et al., 1984; Calzada & Hooz, 1974). Triphenylphosphine was recrystallized from ether/pentane and dried over P2O5 under vacuum before use. Alcohol (1-OH was sublimed at 373–423 K (3 Pa). Equimolar amounts of (1-OH) and triphenylphosphine were flame sealed in a 23 fold molar excess of CCl4 in a 5 mm glass NMR tube under N2. The reaction was followed by 1H NMR spectroscopy. Quantitative conversion was observed after heating for 2 h at 393 K. The literature workup was followed, i.e., addition of pentane, cooling to 273 K, and filtration. The filtrate was concentrated and chromatographed on Florisil, the product eluting in ether. Evaporation of solvent yielded white crystals (72%). Product was purified further by preparative gas chromatography (2 m × 0.5 cm stainless steel, 3% SE-30 on Chrom W NAW, He carrier). White crystals were collected, mp 370–371 K, 1H NMR (300 MHz, CDCl3) δ 1.52–1.56 (m, 2H), 1.74–1.78 (m, 2H), 1.85 (m, 2H), 2.61 (m, 2H), 2.97 (m, 2H), 3.79 (m,1H), 6.06 (t, 2H).

The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Ashby, E. C., DePriest, R. N., Goel, A. B., Wenderoth, B., Pham, T. N. (1984). J. Org. Chem. 49, 3545–3556.

Bertsch, A., Grimme, W., Reinhardt, G., Rose, H., and Warner, P. M. (1988). J. Am. Chem. Soc. 110, 5112–5117.

Calzada, J. G. and Hooz, J. (1974). Organic Syntheses, 54, 63–67.

Fessner, W.-D., Sedelmeier, G., Spurr, P. R., Rihs, G. and Prinzbach, H. (1987). J. Am. Chem. Soc. 109, 4626–4642.

Feiser, L. F. & Feiser, M. (1967). Reagents for Organic Synthesis, Vol. 1, pp 583–584, John Wiley and Sons: New York.

Gassman, P. G. and Marshall, J. L. (1973). Org. Synth. Coll. Vol. V, pp. 91–92, 424–428.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.02746 (2)0.11759 (3)0.317324 (12)0.04828 (8)
O10.30432 (13)0.05847 (19)1.00623 (8)0.0411 (3)
O20.45118 (11)0.0937 (2)0.60835 (8)0.0407 (3)
O30.29321 (10)0.17207 (16)0.67655 (7)0.0281 (3)
C10.29256 (15)0.2448 (2)0.81580 (10)0.0268 (3)
H10.2540 (19)0.352 (3)0.8111 (13)0.037 (6)*
C20.20800 (14)0.0979 (2)0.82345 (10)0.0247 (3)
H20.1442 (18)0.109 (2)0.7871 (12)0.028 (5)*
C30.16542 (15)0.0540 (2)0.90637 (10)0.0295 (4)
H30.1408 (19)0.143 (3)0.9396 (13)0.037 (6)*
C40.07566 (18)0.0844 (3)0.89535 (12)0.0392 (5)
H4A0.037 (2)0.111 (3)0.9421 (14)0.040 (6)*
H4B0.0167 (19)0.056 (3)0.8555 (14)0.038 (6)*
C50.1525 (2)0.2319 (3)0.87059 (13)0.0432 (5)
H5A0.148 (2)0.318 (3)0.9078 (15)0.055 (7)*
H5B0.132 (2)0.277 (3)0.8192 (14)0.046 (6)*
C60.27929 (18)0.1646 (2)0.87042 (11)0.0337 (4)
H60.338 (2)0.238 (3)0.8757 (13)0.041 (6)*
C70.28821 (15)0.0495 (2)0.80002 (10)0.0262 (3)
H70.2616 (16)0.100 (2)0.7532 (11)0.021 (5)*
C80.40863 (15)0.0327 (2)0.78465 (10)0.0277 (3)
H80.4600 (18)0.034 (3)0.7551 (12)0.032 (5)*
C90.45407 (16)0.1045 (2)0.86126 (11)0.0312 (4)
H90.515 (2)0.062 (3)0.8934 (14)0.042 (6)*
C100.38586 (16)0.2291 (2)0.87942 (11)0.0298 (4)
H100.3879 (18)0.295 (3)0.9260 (13)0.034 (5)*
C110.36713 (15)0.1911 (2)0.74588 (10)0.0271 (3)
H110.4299 (19)0.265 (3)0.7347 (12)0.035 (6)*
C120.26467 (16)0.0498 (2)0.93999 (10)0.0312 (4)
C130.34773 (16)0.1254 (2)0.61032 (10)0.0286 (3)
C140.26720 (15)0.1199 (2)0.54091 (10)0.0274 (3)
C150.15020 (17)0.1651 (3)0.54608 (11)0.0337 (4)
H150.121 (2)0.198 (3)0.5945 (14)0.042 (6)*
C160.07909 (19)0.1641 (3)0.47929 (12)0.0378 (4)
H160.001 (2)0.192 (3)0.4831 (15)0.053 (7)*
C170.12596 (18)0.1177 (2)0.40830 (11)0.0337 (4)
C180.2419 (2)0.0714 (3)0.40175 (12)0.0385 (4)
H180.272 (2)0.036 (3)0.3561 (15)0.055 (7)*
C190.31248 (18)0.0719 (3)0.46895 (11)0.0354 (4)
H190.392 (2)0.040 (3)0.4651 (14)0.046 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.07021 (17)0.04111 (12)0.03298 (11)0.00157 (11)0.02163 (10)0.00000 (9)
O10.0454 (8)0.0470 (8)0.0304 (7)0.0117 (7)0.0158 (6)0.0095 (6)
O20.0255 (6)0.0644 (10)0.0322 (7)0.0014 (7)0.0023 (5)0.0046 (7)
O30.0253 (6)0.0376 (7)0.0214 (5)0.0021 (5)0.0005 (4)0.0006 (5)
C10.0290 (8)0.0256 (8)0.0258 (8)0.0016 (7)0.0007 (6)0.0015 (6)
C20.0206 (7)0.0317 (9)0.0218 (7)0.0007 (6)0.0035 (6)0.0012 (6)
C30.0263 (8)0.0385 (10)0.0236 (8)0.0020 (8)0.0037 (6)0.0020 (7)
C40.0311 (9)0.0573 (13)0.0291 (9)0.0142 (9)0.0055 (8)0.0100 (9)
C50.0528 (13)0.0381 (11)0.0384 (11)0.0203 (10)0.0179 (10)0.0109 (9)
C60.0378 (10)0.0283 (8)0.0346 (9)0.0002 (8)0.0146 (8)0.0045 (7)
C70.0275 (8)0.0245 (8)0.0264 (8)0.0004 (7)0.0076 (6)0.0010 (6)
C80.0234 (8)0.0327 (9)0.0270 (8)0.0049 (7)0.0036 (6)0.0041 (7)
C90.0256 (8)0.0392 (10)0.0287 (8)0.0035 (8)0.0068 (7)0.0000 (7)
C100.0314 (9)0.0320 (9)0.0259 (8)0.0069 (7)0.0026 (7)0.0037 (7)
C110.0234 (8)0.0330 (9)0.0249 (8)0.0029 (7)0.0010 (6)0.0007 (7)
C120.0324 (9)0.0339 (9)0.0271 (8)0.0099 (8)0.0080 (7)0.0069 (7)
C130.0273 (8)0.0332 (9)0.0255 (8)0.0027 (7)0.0032 (6)0.0002 (7)
C140.0288 (8)0.0292 (8)0.0241 (7)0.0024 (7)0.0002 (6)0.0002 (6)
C150.0326 (9)0.0415 (10)0.0269 (8)0.0042 (8)0.0016 (7)0.0033 (8)
C160.0363 (10)0.0439 (11)0.0332 (9)0.0062 (9)0.0066 (8)0.0036 (8)
C170.0467 (11)0.0276 (8)0.0264 (8)0.0036 (8)0.0094 (7)0.0001 (7)
C180.0480 (12)0.0425 (10)0.0250 (8)0.0041 (9)0.0038 (8)0.0064 (8)
C190.0338 (10)0.0417 (10)0.0307 (9)0.0007 (9)0.0039 (7)0.0059 (8)
Geometric parameters (Å, º) top
Br1—C171.8989 (18)C6—C71.532 (3)
O1—C121.210 (2)C6—H60.91 (2)
O2—C131.208 (2)C7—C81.556 (2)
O3—C131.348 (2)C7—H70.944 (19)
O3—C111.448 (2)C8—C91.516 (2)
C1—C101.512 (2)C8—C111.537 (3)
C1—C111.534 (2)C8—H80.95 (2)
C1—C21.557 (2)C9—C101.328 (3)
C1—H10.99 (2)C9—H90.94 (2)
C2—C31.538 (2)C10—H100.96 (2)
C2—C71.577 (2)C11—H110.96 (2)
C2—H20.95 (2)C13—C141.486 (2)
C3—C121.525 (3)C14—C151.388 (3)
C3—C41.545 (3)C14—C191.390 (3)
C3—H30.97 (2)C15—C161.386 (3)
C4—C51.561 (3)C15—H150.93 (2)
C4—H4A0.94 (2)C16—C171.379 (3)
C4—H4B0.98 (2)C16—H160.93 (3)
C5—C61.548 (3)C17—C181.381 (3)
C5—H5A0.95 (3)C18—C191.388 (3)
C5—H5B0.97 (2)C18—H180.90 (3)
C6—C121.526 (3)C19—H190.95 (2)
C13—O3—C11116.12 (13)C9—C8—C1197.73 (14)
C10—C1—C1197.88 (14)C9—C8—C7108.66 (14)
C10—C1—C2107.69 (14)C11—C8—C7100.16 (13)
C11—C1—C2100.82 (14)C9—C8—H8118.3 (12)
C10—C1—H1116.2 (13)C11—C8—H8117.0 (13)
C11—C1—H1116.5 (13)C7—C8—H8112.7 (13)
C2—C1—H1115.4 (13)C10—C9—C8107.93 (16)
C3—C2—C1117.55 (14)C10—C9—H9125.5 (14)
C3—C2—C7103.82 (14)C8—C9—H9126.2 (14)
C1—C2—C7102.75 (13)C9—C10—C1107.99 (15)
C3—C2—H2111.7 (12)C9—C10—H10128.5 (13)
C1—C2—H2110.0 (12)C1—C10—H10123.3 (13)
C7—C2—H2110.4 (12)O3—C11—C1109.80 (13)
C12—C3—C2103.59 (14)O3—C11—C8115.40 (14)
C12—C3—C496.62 (15)C1—C11—C894.89 (14)
C2—C3—C4106.21 (15)O3—C11—H11109.6 (12)
C12—C3—H3115.2 (13)C1—C11—H11113.0 (13)
C2—C3—H3116.8 (13)C8—C11—H11113.5 (13)
C4—C3—H3115.8 (13)O1—C12—C3130.44 (19)
C3—C4—C5103.82 (16)O1—C12—C6129.82 (19)
C3—C4—H4A112.7 (14)C3—C12—C698.47 (14)
C5—C4—H4A108.2 (14)O2—C13—O3123.00 (16)
C3—C4—H4B110.6 (14)O2—C13—C14124.38 (16)
C5—C4—H4B112.7 (14)O3—C13—C14112.61 (15)
H4A—C4—H4B108.8 (19)C15—C14—C19119.94 (17)
C6—C5—C4104.24 (16)C15—C14—C13121.73 (16)
C6—C5—H5A108.9 (15)C19—C14—C13118.31 (16)
C4—C5—H5A111.8 (16)C16—C15—C14119.93 (18)
C6—C5—H5B110.1 (14)C16—C15—H15120.6 (14)
C4—C5—H5B114.3 (14)C14—C15—H15119.5 (14)
H5A—C5—H5B107 (2)C17—C16—C15119.25 (19)
C12—C6—C7103.11 (15)C17—C16—H16121.0 (15)
C12—C6—C596.41 (17)C15—C16—H16119.7 (16)
C7—C6—C5107.16 (15)C16—C17—C18121.88 (18)
C12—C6—H6115.2 (14)C16—C17—Br1118.71 (16)
C7—C6—H6115.7 (15)C18—C17—Br1119.41 (15)
C5—C6—H6116.8 (15)C17—C18—C19118.57 (18)
C6—C7—C8117.96 (14)C17—C18—H18122.4 (16)
C6—C7—C2103.82 (15)C19—C18—H18119.0 (16)
C8—C7—C2102.70 (13)C18—C19—C14120.42 (19)
C6—C7—H7111.1 (11)C18—C19—H19119.2 (14)
C8—C7—H7109.0 (12)C14—C19—H19120.4 (14)
C2—C7—H7111.8 (11)
C10—C1—C2—C345.9 (2)C10—C1—C11—O3171.73 (14)
C11—C1—C2—C3147.84 (15)C2—C1—C11—O361.93 (16)
C10—C1—C2—C767.36 (16)C10—C1—C11—C852.49 (15)
C11—C1—C2—C734.62 (15)C2—C1—C11—C857.31 (14)
C1—C2—C3—C1283.66 (18)C9—C8—C11—O3167.03 (14)
C7—C2—C3—C1228.96 (17)C7—C8—C11—O356.39 (17)
C1—C2—C3—C4175.17 (15)C9—C8—C11—C152.38 (15)
C7—C2—C3—C472.21 (17)C7—C8—C11—C158.25 (14)
C12—C3—C4—C535.88 (17)C2—C3—C12—O1143.5 (2)
C2—C3—C4—C570.38 (18)C4—C3—C12—O1108.0 (2)
C3—C4—C5—C60.47 (19)C2—C3—C12—C648.63 (17)
C4—C5—C6—C1235.09 (18)C4—C3—C12—C659.86 (16)
C4—C5—C6—C770.79 (19)C7—C6—C12—O1142.0 (2)
C12—C6—C7—C880.40 (19)C5—C6—C12—O1108.6 (2)
C5—C6—C7—C8178.53 (16)C7—C6—C12—C349.99 (17)
C12—C6—C7—C232.36 (17)C5—C6—C12—C359.33 (16)
C5—C6—C7—C268.70 (18)C11—O3—C13—O23.2 (3)
C3—C2—C7—C62.08 (16)C11—O3—C13—C14176.03 (14)
C1—C2—C7—C6125.03 (14)O2—C13—C14—C15176.83 (19)
C3—C2—C7—C8121.31 (14)O3—C13—C14—C152.3 (3)
C1—C2—C7—C81.64 (15)O2—C13—C14—C191.4 (3)
C6—C7—C8—C948.8 (2)O3—C13—C14—C19179.39 (17)
C2—C7—C8—C964.60 (17)C19—C14—C15—C160.7 (3)
C6—C7—C8—C11150.60 (16)C13—C14—C15—C16177.53 (19)
C2—C7—C8—C1137.21 (15)C14—C15—C16—C170.1 (3)
C11—C8—C9—C1034.21 (18)C15—C16—C17—C180.2 (3)
C7—C8—C9—C1069.31 (19)C15—C16—C17—Br1179.83 (16)
C8—C9—C10—C10.1 (2)C16—C17—C18—C190.1 (3)
C11—C1—C10—C934.40 (19)Br1—C17—C18—C19179.83 (16)
C2—C1—C10—C969.67 (19)C17—C18—C19—C140.7 (3)
C13—O3—C11—C1179.81 (15)C15—C14—C19—C181.1 (3)
C13—O3—C11—C874.45 (19)C13—C14—C19—C18177.24 (18)
Comparison of the angles (°) between least-squares planes in 1-OPBB and related compounds top
Planes 1-6 are defined by atoms C1-C11-C8, C8-C9-C10-C1, C1-C2-C7-C8, C2-C3-C6-C7, C3-C12-C6, and C3-C4-C5-C6, respectively.
1-OPBB3-OPBB4-OPBB1-OCH323-OCH32
Plane1-Plane2124.4 (1)121.7 (3)122.9 (3)126.9 (2)125.7 (1)
Plane1-Plane3121.5 (1)122.5 (3)120.4 (3)119.6 (1)119.3 (1)
Plane2-Plane3114.2 (1)115.8 (2)116.7 (1)113.5 (1)115.1 (1)
Plane3-Plane4123.2 (1)125.3 (2)128.1 (2)122,9(1)125.2 (1)
Plane4-Plane5130.6 (1)129.6 (4)129.4 (2)130.8 (2)130.3 (2)
Plane4-Plane6111.5 (1)110.6 (2)109.8 (2)111.6 (1)109.8 (1)
Plane5-Plane6118.0 (1)119.9 (3)120.8 (2)117.6 (1)119.9 (2)
 

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