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- 11 According to our competition experiment
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9 Typical procedure for Equation
[2]
: The degassed solution
of ethyl 4-iodobutyrate (4, 48 mg, 0.20
mmol), p-toluene-sulfonyl cyanide (2, 46 mg, 0.24 mmol) and hexamethylditin (79
mg, 0.24 mmol) in benzene (1 mL) was irradiated under 300 nm UV
lamp at room temperature for 2 h. The solvent was evaporated under
reduced pressure and the residue was chromatographed on a silica
gel column (n-hexane/ethyl acetate = 1:5)
to yield ethyl 4-cyanobutyrate (5, 25 mg,
0.18 mmol, 88% yield). 1H NMR (CDCl3,
300 MHz) δ 1.21 (t,
J = 7.1
Hz, 3 H), 1.87-1.97 (m, 2 H), 2.38-2.44 (m, 4
H), 4.09 (q, J = 7.1 Hz, 2 H); 13C
NMR (CDCl3, 100 MHz) δ 14.0, 16.4, 20.6, 32.3,
60.6, 118.9, 171.8; IR (NaCl) 2994, 2950, 2880, 2365, 2344, 2252,
1734, 1458, 1378, 1222, 1198, 1028 cm-1.
13 Typical procedure for Equation
[6]
: The degassed solution of 4-phenoxybutyl
phenyl telluride (13, 65 mg, 0.18 mmol), p-toluenesulfonyl cyanide (2, 70 mg, 0.37 mmol), methyl allyl sulfone
(6, 44 mg, 0.37 mmol) and V-40 (9 mg, 0.037
mmol) in t-butylbenzene (1 mL) was stirred
at 140 °C under N2 for 12 h. The solvent was
evaporated under reduced pressure and the residue was chromatographed
on a silica gel column (n-hexane/ethyl
acetate = 1:10) to yield 5-phenoxy pentanenitrile (29 mg,
0.16 mmol, 89% yield). 1H NMR (CDCl3,
300 MHz) δ 1.85-1.95 (m, 4 H), 2.41-2.45
(t,
J = 6.7 Hz, 2
H), 3.98-4.00 (t, J = 5.7
Hz, 2 H), 6.85-6.92 (d, J = 5.6
Hz, 2 H), 6.93-6.95 (t, J = 7.3
Hz, 1 H), 7.23-7.28 (m, 2 H); 13C
NMR (CDCl3, 100 MHz) δ 16.6, 22.0, 27.8, 66.0,
113.9, 119.0, 120.4, 129.0, 158.2; IR (NaCl) 2946, 2877, 2362, 2343,
2247, 1600, 1498, 1245 cm-1.
