References
Selected examples:
1a
Trofimov BA.
Gusarova NK.
Malysheva SF.
Ivanova NI.
Sukhov BG.
Belogorlova NA.
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1b
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1c
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1d
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1e
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2a
Jessop CM.
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2b
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Parsons AF.
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3 Pantazis, D.; McGrady, J. E. unpublished results.
4a
Semenzin D.
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Albouy D.
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5
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6 Performed in a CEM Focused Microwave Synthesis System.
7 All new compounds gave consistent spectral and HRMS data.
8
Typical Procedure.
To diphenylphosphine sulfide (0.327 g, 3 equiv, 1.5 mmol) in a N2 flushed flask was added non-degassed dioxane (2 mL), followed by methyl methacrylate (0.053 mL, 0.5 mmol). Then, Et3B (1 M solution in hexane, 0.15 mL, 0.3 equiv, 0.15 mmol) was added and the reaction was left to stir for 4 h. After this time a further portion of Et3B (1 M solution in hexane, 0.15 mL, 0.3 equiv, 0.15 mmol) was added, and the mixture was left to stir for 16 h. The reaction mixture was then concentrated in vacuo to afford the crude product. Following column chromatography (4:1, PE-EtOAc), methyl 3-(diphenylphosphorothioyl)-2-methylpropanoate (9) was isolated as a colourless oil (0.147 g, 92%); R
f
= 0.2 (4:1, PE-EtOAc). IR (thin film): νmax = 3054 (m), 2975 (m), 2949 (m), 1731 (s, C=O), 1436 (s, P-Ph), 1309 (m), 1274 (m), 1211 (s), 1158 (s), 1102 (s), 1027 (m), 998 (m) cm-1.
1H NMR (400 MHz, CDCl3): δ = 7.91-7.80 (4 H, m, 4 × CH Ar), 7.54-7.41 (6 H, m, 6 × CH Ar), 3.46 (3 H, s, O-CH
3), 3.21-3.08 [2 H, m, P(S)CH
2-CH], 2.52-2.41 [1 H, m, P(S)CH2-CH], 1.18 (3 H, d, J = 7 Hz, CH2-CH-CH
3).
13C NMR (100.6 MHz, CDCl3): δ = 175.8 (d, 3
J
C-P = 9.5 Hz, O=C-O-CH3), 133.1 (d, 1
J
C-P = 80.5 Hz, C
q Ar), 132.3 (d, 1
J
C-P = 80.5 Hz, C
q Ar), 131.6 (d, 4
J
C-P = 3.0 Hz, CH Ar), 131.5 (d, 4
J
C-P = 3.0 Hz, CH, Ar), 131.3 (d, 2
J
C-P = 10.5 Hz, 2 × CH Ar), 131.0 (d, 2
J
C-P 10.0 Hz, 2 × CH Ar), 128.7 (d, 3
J
C-P 12.0 Hz, 2 × CH Ar), 128.5 (d, 3
J
C-P = 12.0 Hz, 2 × CH Ar), 51.9 (O-CH3), 35.5 [d, 1
J
C-P = 57 Hz, P(S)CH2], 34.3 [d, 2
J
C-P = 1 Hz, P(S)CH2-CH], 19.4 (d, 3
J
C-P = 8.5 Hz, CH2-CH-CH3). 31P NMR (161.9 MHz, CDCl3): δ = 41.3 [Ph2
P(S)]. MS (CI, NH3): m/z (%) = 319 (100), 218 (17). HRMS: m/z calcd for C17H19O2PS: [M + H+] 319.0922 (0.2 ppm); found: [M + H+] 319.0921.
9 Deprotonation of Ph2P(S)H and addition to electron-poor alkenes has been reported previously (see ref. 4).
For some recent examples see:
10a
Daniewski AR.
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10b
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10c
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11a
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11c
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11d
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11e
Green IR.
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11f
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11g
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11h
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Nambudiry MEN.
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11i
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Deprotonation of alkyl(diphenyl)phosphine sulfides and reaction with MeI or CO2 has been reported. See:
12a
Yoshifuji M.
Ishizuka T.
Choi YJ.
Inamoto N.
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1984,
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12b
Savignac M.
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13 See for example: Gilbertson SR.
Chang C.-WT.
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