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34249823764
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Satisfactory spectral and LC-MS or HRMS analytical data were obtained for all new compounds. A typical experiment is outlined as follows: To a solution of α-cyano ketone 1 (110 mg, 0.55 mmol) in THF (10 mL) at -40°C was added LN (7.5 mL, 0.365 M, 2.75 mmol) dropwise. The resulting dark green solution was stirred at the same temperature for 20 min followed by addition of phenylselenyl bromide (156 mg, 0.66 mmol) in one portion. The resulting mixture was continued to stir for additional 30 min at -40°C and then quenched with sat. aq NH4Cl and extracted with EtOAc (2 x 10 mL, The combined extracts were washed with brine, dried with Na2SO4, and concentrated to give the crude residue, which was subjected to flash chromatography on silica gel (EtOAc-n-hexane, 1:50) to afford the corresponding α-phenylseleno ketone 2 as a colorless oil (165 mg, 90, IR (neat, 1729, 1604, 1577 cm-1. 1HNMR 300 MHz, CDCl
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34249782083
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1-Benzoyl-4,6,6-trimethylcyclohex-3-enecarbonitrile (10, IR (KBr, 2232, 1692, 1596, 1578 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.12 (s, 3 H, 1.21 (s, 3 H, 1.72 (br s, 3 H, 1.96 (d, J, 17.9 Hz, 1 H, 2.31 (d, J, 17.9 Hz, 1 H, 2.58 (br d, J, 17.8 Hz, 1 H, 2.90 (br d, J, 17.8 Hz. 1 H, 5.32 (br s, 1 H, 7.42-7.48 (tm, J, 7.3 Hz. 2 H) 7.52-7.58 (tm, J, 7.3 Hz, 1 H, 8.04-8.08 (dm, J, 7.3 Hz, 2 H, 13C NMR (75 MHz, CDCl3, δ, 22.7, 23.8, 27.7, 33.1, 36.7, 44.0, 53.2, 115.2, 121.7,128.4, 129.1, 132.9, 133.9, 137.5, 195.3. LC-MS (ES, m/z, 253 [M, 1-Benzoyl-3,4,6,6-tetramethylcyclohex-3-enecarbonitrile (11, IR (KBr, 2232, 1692, 1595, 1578 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.08 (s, 3 H, 1.20 (s, 3 H, 1.66 (br s, 6 H, 1.90 (d, J, 17.8 Hz, 1 H, 2.38 br d, J, 18.0 Hz, 1 H
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2 containing a small portion of pyridine at 25°C gave rise to a mixture of the exo- and endocyclic enones in a ratio of 1:1.3.
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2 containing a small portion of pyridine at 25°C gave rise to a mixture of the exo- and endocyclic enones in a ratio of 1:1.3.
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