1074
W. Li et al. / Tetrahedron Letters 45 (2004) 1071–1074
2
7
H), 7.90 (d, J ¼ 8:3 Hz, 2H), 7.77 (d, J ¼ 7:8 Hz, 2H),
Yamaguchi, M. Bull. Chem. Soc. Jpn. 1981, 54, 2221; (d)
Suzuki, S.; Onishi, T.; Fujita, Y.; Misawa, H.; Otera, J.
Bull. Chem. Soc. Jpn. 1986, 59, 3287; (e) Barbry, D.;
Champagne, P. Tetrahedron Lett. 1996, 43, 7725; (f)
Chandrasekhar, S.; Sridhar, M. Tetrahedron Lett. 2000,
13
.53 (d, J ¼ 7:8 Hz, 2H), 7.46 (t, J ¼ 7:4 Hz, 1H);
C
NMR d 192.97, 146.21, 139.15, 135.46, 130.48 (2C),
1
observed [M+H] 183.16 (calcd 183.08).
29.45 (2C), 128.91, 127.68 (2C), 127.46 (2C); LC-ESMS
þ
4
1, 5423; (g) For other oxidizing reagents, see: Hass, H. B.;
Bender, M. L. J. Am. Chem. Soc. 1949, 71, 1767; (h) Das,
S.; Panigrahi, A. K.; Maikap, G. C. Tetrahedron Lett.
2
003, 44, 1375, and references cited therein.
Supplementary data
8. (a) Kornblun, N.; Powers, J. W.; Anderson, G. J.; Jones,
W. J.; Larson, H. O.; Levand, O.; Weaver, W. M. J. Am.
Chem. Soc. 1957, 79, 6562; (b) Kornblun, N.; Jones, W. J.;
Anderson, G. J. J. Am. Chem. Soc. 1959, 81, 4113; (c)
Ganem, B.; Boekman, R. K. Tetrahedron Lett. 1974, 15,
Typical experimental procedures for the preparation of
aldehydes with supporting analytical data. The supple-
mentary data is available online with the paper in
ScienceDirect.
9
17; (d) Ghera, E.; Plementitas, A.; Ben-David, Y.
Synthesis 1984, 504; (e) Maslak, P.; Narvaez, J. N.; Kula,
J.; Malinski, D. S. J. Org. Chem. 1990, 55, 4550.
. Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1990, 34,
9
4
825.
Acknowledgements
10. For a review, see Tidwell, Y. T. Org. React. 1990, 39, 297;
See also: (a) Pfitzner, K. E.; Moffatt, J. G. J. Am. Chem.
Soc. 1965, 87, 5661, 5670; (b) Pfitzner, K. E.; Moffatt, J.
G. J. Am. Chem. Soc. 1966, 88, 1762; (c) Epstein, W. W.;
Sweat, F. W. Chem. Rev. 1967, 67, 247; (d) Albright, J. D.;
Goldman, L. J. Am. Chem. Soc. 1967, 89, 2416; (e) Parikh,
J. R.; von Doering, W. J. Am. Chem. Soc. 1967, 89, 5505;
The authors wish to thank Walter Massefski, Nelson
Huang, Ying Ge, and Jim Bourassa for their analytical
chemistry supports and Andre Asselin for support.
(
9
f) Corey, E. J.; Kim, C. U. Tetrahedron Lett. 1973, 14,
19; (g) Albright, J. D. J. Org. Chem. 1974, 39, 1977; (h)
Omura, K.; Sharma, A.; Swern, D. J. Org. Chem. 1976, 41,
57; (i) Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
References and notes
9
1
. Nicolaou, K. C.; Baran, S.; Zhong, Y. J. Am. Chem. Soc.
001, 123, 3183.
. Li, W. S.; Liu, L. K. Synthesis 1989, 293, 7881.
. Ohkubo, K.; Fukuzumi, S. Org. Lett. 2000, 2, 3647.
. Potthast, A.; Roseenau, T.; Chen, C. L.; Gratzl, S. J. Org.
Chem. 1995, 60, 4320.
11. (a) Peterson, K. P.; Larock, B. C. J. Org. Chem. 1998, 63,
3185; (b) Arterburn, J. B.; Perry, M. C. Org. Lett. 1999, 5,
769; (c) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am.
Chem. Soc. 2002, 124, 766; (d) Coleman, K. S.; Bedel, L. J.
L.; Osborn, J. A. C.R. Acad. Sci., Ser. IIC––Chem. 2000,
3, 765, and references cited therein.
2
2
3
4
5
. Selected literature: (a) Langer, O.; Dolle, F.; Valette, H.;
Halldin, C.; Vaufrey, F.; Fuseau, C.; Coulon, C.; Ottavi-
ani, M.; N ꢀa gren, K.; Bottlaender, M.; Mazi ꢁe re, B.;
Crouzel, C. Bioorg. Med. Chem. 2001, 9, 677; (b) Chung,
S. J.; Kim, D. H. Tetrahedron 1995, 51, 12549; (c)
Goodman, M. S.; Hamilton, A. D.; Weiss, J. J. Am.
Chem. Soc. 1995, 117, 8447; (d) Adediran, S. A.; Cabaret,
D.; Drouillat, B.; Pratt, R. F.; Wakselman, M. Bioorg.
Med. Chem. 2001, 9, 1175.
12. (a) Johnson, C. R.; Jones, M. P. J. Org. Chem. 1967, 32,
2014; (b) Johnson, C. R.; Rigau, J. J. J. Am. Chem. Soc.
1969, 91, 5398; (c) Khuddus, M. A.; Swern, D. J. Am.
Chem. Soc. 1973, 95, 8393; (d) Zhang, J.; Saito, S.;
Koizumi, T. J. Org. Chem. 1998, 63, 5265; (e) Smith, G.;
Winstein, S. Tetrahedron 1958, 3, 317.
1
13. Analytical data for bromodimethylsulfonium bromide: H
1
3
2 2 3
NMR d (400 MHz, CD Cl ) 2.66 (s, –CH ), C NMR
d 27.12. MS: only the cation fragment was observed
þ
6
. Selected literature: (a) Semmelhack, M. F.; Ho, S.; Cohen,
D.; Steigerwad, M.; Lee, M. C.; Lee, G.; Gilbert, A. M.;
Wufll, W. D.; Ball, R. G. J. Am. Chem. Soc. 1994, 116,
(calcd for C
2
H
6
SBr : 140.94, observed: 140.82). Also
see Megyeri, G.; Keve, T. Synth. Commun. 1989, 19,
3415.
7
108; (b) Shamblee, D. A.; Gillespie, S. G., Jr. J. Med.
14. A footnote in a report mentioned the conversion of benzal
bromides into aldehydes by hydrolysis. Such study was
Chem. 1979, 22, 86; (c) Blicke, F. F.; Patelski, R. A. J. Am.
Chem. Soc. 1936, 58, 559; (d) Khatuya, H. Tetrahedron
Lett. 2001, 42, 2643; (e) Angelini, G.; Giancaspro, C.;
Illuminati, G.; Sleiter, G. J. Org. Chem. 1980, 45, 1786.
. For N-oxides as oxidants, see: (a) Feely, W.; Lehn, W. M.;
Boekelheide, V. J. Org. Chem. 1957, 22, 1135; (b) Franzen,
V. Org. Synth. 1973, 5, 872; (c) Mukaiyama, S.; Inanga, J.;
carried out in the presence of K
for 1 day. The authors attributed the conversion of the
benzal bromides as the result of hydrolysis by water
2
CO
3
(d
6
-DMSO) at 60 ꢁC
7
2 3
generated from the K CO . Apparently, DMSO here was
intentionally used as NMR solvent. Xu, H.; Gibb, C. L.
D.; Gibb, B. C. J. Org. Chem. 1999, 64, 9286.