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3.27e3.40 (m, 2H, eCHeOD); dC (ppm; 75.5 MHz; CD3OD) 10.39
(eCH3), 30.510 (eCH2), 75.32(eCHeOD).
5.4.7. Cyclohexanol (2g)27,34. Colorless liquid, dH (ppm; 300 MHz;
CD3OD) 0.92 (td, J¼7.5 Hz, 6H, eCH3), 1.31e1.56 (m, 4H, eCH2),
3.27e3.40 (m, 2H, eCHeOD); dC (ppm; 75.5 MHz; CD3OD) 10.39
(eCH3), 30.510 (eCH2), 75.32(eCHeOD).
5.4.8. Phenylmethanol (2h)27,35,36. Colorless liquid, dH (ppm;
300 MHz; CD3OD) 4.59 (s, 2H, eCH2), 7.15e7.50 (m, 4H); dC (ppm;
75.5 MHz; CD3OD) 65.23 (eCH2), 127.97, 128.23, 129.32, 142.67.
5.4.9. Naphthalen-1-ylmethanol (2i)27,32,36. Colorless liquid, dH
(ppm; 300 MHz; CD3CN) 3.28 (br, 1H, eCH2eOH), 5.10 (s, 2H,
CH2eOH), 7.48e7.60 (m, 4H), 7.85e7.96 (m, 2H), 8.13e8.18 (m, 1H);
dC (ppm; 75.5 MHz; CD3CN) 62.98, 124.71, 125.62, 126.45, 126.66,
126.90, 128.63, 129.34, 132.06, 134.60, 137.16.
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5.4.10. 4-(Hydroxymethyl)benzonitrile (2j)27. White solid, dH (ppm;
300 MHz; CD3CN) 4.93 (s, 2H, eCH2eOe), 7.50e7.53 (m, 2H),
7.66e7.69 (m, 2H); dC (ppm; 75.5 MHz; CD3CN) 63.85 (eCH2eOe),
111.18, 119.84 (eCN), 127.87, 130.08, 148.74.
2058e2062.
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5.4.11. (4-Methoxyphenyl)methanol (2k)32
. dH (ppm; 300 MHz;
CD3OD) 3.75 (s, 3H, eCH3), 4.51 (s, 2H, eCH2), 6.87 (d, J¼9 Hz, 2H),
7.26 (d, J¼9 Hz, 2H); dC (ppm; 75.5 MHz; CD3OD) 55.68 (eCH3),
64.93 (eCH2eOD), 114.72, 129.61, 134.69, 160.47.
10. Multiple NMR spectra and the structure of the adduct was discussed in detail in
the Supplementary dataSupplementary data.
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5.4.12. (4-(Dimethylamino)phenyl)methanol (2l)36. White solid, dH
(ppm; 300 MHz; CD3CN) 2.94 (s, 6H, eN(CH3)2), 3.65 (s, 1H,
eCH2eOH), 4.48 (s, 2H, eCH2eOH), 6.74e6.78 (m, 2H), 7.18e7.23
(m, 2H); dC (ppm; 75.5 MHz; CD3CN) 40.95 (eN(CH3)2), 64.75
(eCH2eOe), 113.38, 129.15, 129.95, 150.92.
Acknowledgements
We are grateful to the Swiss National Science Foundation and
the University of Zurich for financial support.
Supplementary data
17. Brown, H. C.; Schlesinger, H. I.; Burg, A. B. J. Am. Chem. Soc. 1939, 61, 673e680.
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Supplementary data associated with this article can be found, in
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