product 2,2-diphenylacetaldehyde dimethyl acetal (240 mg, 98%)
as a colourless oil; nmax (film)/cm-1 (neat) 2970, 1720, 1431, 1109,
1057 and 745; 1H NMR (400 MHz; CDCl3) d = 7.33–7.06 (10H,
m), 4.91 (1H, d, J = 8 Hz), 4.15 (1H, d, J = 8 Hz) 3.21 (6H,
s); 13C NMR (100 MHz; CDCl3) d = 141.6, 129.7, 128.9, 126.2,
106.9, 55.0 and 54.5; MS (CI) m/z 260 (M + NH4)+; HRMS (ES)
calculated for C16H22NO2 (M + NH4)+, 260.1645; found (M +
NH4)+ 260.1644.
7 (a) M. W. C. Robinson, R. Buckle, I. Mabbett, G. M. Grant and
A. E. Graham, Tetrahedron Lett., 2007, 48, 4723–4725; (b) M. W. C.
Robinson, D. A. Timms, S. M. Williams and A. E. Graham, Tetrahedron
Lett., 2007, 48, 6249–6251.
8 E. G. Lewers, in Comprehensive Heterocyclic Chemistry, Vol 7, ed. A.
R. Katritzky, C. W. Rees and W. Lwowski, Pergamon, Oxford, 1984,
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9 (a) K. Iwanami, J.-C. Choi, B. Lu, T. Sakakura and H. Yasuda, Chem.
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Srinivas, V. Radha Rani, S. J. Kulkarni and K. V. Raghavan, J. Mol.
Catal. A: Chem., 2002, 179, 221–231.
2,2-Diphenylacetaldehyde diethyl acetal29. (96% yield); nmax
10 B. D. G. Williams and M. Lawton, Org. Biomol. Chem, 2005, 3, 3269–
(film)/cm-1 (neat) 2975, 1727, 1496, 1451, 1113, 1057, 745 and
3272.
1
696; H NMR (400 MHz; CDCl3) d = 7.26–7.06 (10H, m), 4.99
11 (a) K. Maruoka, O. Takashi and H. Yamamoto, Tetrahedron, 1992, 48,
3303–3312; (b) X.-M. Deng, X.-L. Sun and Y. Tang, J. Org. Chem.,
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U. Jana, J. Org. Chem., 1998, 63, 8212–8216.
12 R. A. Sheldon, J. A. Ealing, S. K. Lee, H. E. B. Lempers and R. S.
Downing, J. Mol. Catal. A: Chem., 1998, 134, 129–135.
13 (a) R. van Grieken, D. P. Serrano, J. A. Melero and A. Garc´ıa, J. Mol.
Catal. A: Chem., 2004, 222, 167–174; (b) D. P. Serrano, R. van Grieken,
J. A. Melero and A. Garc´ıa, Appl. Catal. A, 2004, 269, 137–146.
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(1H, d, J = 8 Hz), 4.15 (1H, d, J = 8 Hz), 3.59–3.49 (2H, m),
3.39–3.31 (2H, m), 0.98 (6H, t, J = 7 Hz); 13C NMR (100 MHz;
CDCl3) d = 141.9, 129.3, 128.4, 126.6, 105.2, 62.8, 55.8, 15.5; MS
(ES) m/z 288 (M + NH4)+; HRMS (ES) calculated for C18H26NO2
(M + NH4)+, 288.1958; found (M + NH4)+ 288.1958.
2-Phenylpropionaldehyde dimethyl acetal30. (80% yield); nmax
(film)/cm-1 (neat) 2935, 1605, 1452, 1058, 760 and 698; 1H NMR
(CDCl3, 400 MHz) d = 7.37–7.05 (5H, m), 4.29 (1H, d, J = 7 Hz),
3.29 (3H, s), 3.16 (3H, s), 2.93 (1H, pent, J = 7 Hz), 1.20 (3H, d,
J = 7 Hz); 13C NMR (CDCl3, 100 MHz) d = 142.1, 127.4, 126.9,
125.1, 107.6, 53.5, 53.0, 41.9, 15.8; MS (ES) m/z 198 (M + NH4)+.
15 (a) P. J. Kocienski, Protecting Groups, Thieme, New York, 2003; (b) M.
A. F. M. Rahman and Y. Jahng, Eur. J. Org. Chem., 2007, 379–383;
(c) A. E. Graham, Synth. Commun., 1999, 29, 697–703.
16 (a) The synthesis of acetals by tandem processes has been described in a
limited number of cases; for the synthesis of unstable o-benzoquinone
monodimethyl acetals by oxidation of 2-methoxyphenols in methanol
with (diacetoxy)iodobenzene (DAIB) or [bis(trifluoroacetoxy)]-
iodobenzene (BTIB) see C.-S. Chu, T.-H. Lee, P. D. Rao, L.-D. Song
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Y.-L. Shen, N. S. Kameswara Rao and C.-C. Liao, J. Org. Chem.,
2002, 67, 8157–8165; for rhodium-catalyzed tandem hydroformyla-
tion/acetalization reactions see R. Roggenbuck, A. Schmidt and P.
Eilbracht, Org. Lett, 2002, 4, 289–291.
17 (a) L. F. Tietze, Chem. Rev., 1996, 96, 115–136; (b) R. J. K. Taylor, M.
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L. Wei, A. E. Taylor and A. E. Graham, Tetrahedron, 2007, 63, 10528–
10533; (e) B. M. Smith and A. E. Graham, Tetrahedron Lett., 2007, 48,
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18 (a) J. Louie, C. W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001,
123, 11312–11313; (b) C. W. Bielawski, J. Louie and R. H. Grubbs, J.
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19 Y. Tamura, T. Kawasaki, H. Yasuda, N. Gohda and Y. Kita, J. Chem.
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20 P. C. B. Page, B. R. Buckley, G. A. Rassias and A. J. Blacker, Eur. J.
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23 K Jeyakumar and D. K. Chand, Synlett, 2008, 807–819.
24 K. A. Monk, N. C. Duncan, E. A. Bauch and C. M. Garner,
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Acknowledgements
The authors thank the Engineering and Physical Sciences Research
Council (EPSRC) and Cardiff University for financial support, the
EPSRC National Mass Spectrometry Service, Swansea University,
the EPSRC Solid-State NMR Service, Durham University and
Mr Peter Davies (School of Engineering, Swansea University).
The authors are indebted to Dr N. C. O. Tomkinson (Cardiff
University) and Dr S. D. Kean (University of Glamorgan) for
their continued advice, support and inspiration.
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