PAPER
2,2-Dichloroaldehydes via Chlorination of Aldehydes or Alcohols
2177
MS (EI): m/z (%) = 81 (100), 86 (62), 89 (41), 91 (39), 112 (51), 117
(16) (a) Bellesia, F.; De Buyck, L.; Ghelfi, F. Synlett 2000, 146.
+
(
60), 153 (3) (M – 29).
(b) De Buyck, L.; Verhè, R.; De Kimpe, N.; Courtheyn, D.;
Schamp, N. Bull. Soc. Chim. Belg. 1980, 89, 441. (c) De
Buyck, L.; Casaert, F.; De Lepeleire, C.; Schamp, N. Bull.
Soc. Chim. Belg. 1988, 97, 525. (d) Bellesia, F.; De Buyck,
L.; Ghelf, F.; Pagnoni, U. M.; Strazzolini, P. submitted for
publication .
Anal. Calcd for C H Cl O: C, 45.92; H, 6.61. Found: C, 45.8; H,
7
12
2
6
.8.
,2-Dichloro-decanal (3h)16c
2
Colorless liquid; bp 61–63 °C/ 0.03 mmHg.
(17) (a) Ghelfi, F.; Parsons, A. F. J. Org. Chem. 2000, 65, 6249.
–
1
IR (film): 1748 (C=O) cm .
(
b) Ghelfi, F.; Bellesia, F.; Forti, L.; Ghirardini, G.; Grandi,
1
R.; Libertini, E.; Montemaggi, M. C.; Pagnoni, U. M.;
Pinetti, A.; De Buyck, L.; Parsons, A. F. Tetrahedron 1999,
H NMR (CDCl ): d = 0.88 (t, 3 H, J = 6.4 Hz), 1.00–1.80 (6 H, m),
3
1
.54–1.80 (2 H, m), 2.22–2.38 (2 H, m), 9.27 (1 H, s).
55, 5839.
MS (EI): m/z (%): 95 (100), 100 (46), 112 (33), 131 (25), 167 (4)
(
(
18) Ghelfi, F.; Stevens, C. V.; De Buyck, L.; Laureyn, I.; Van
Meenen, E.; Rogge, T. M.; Nikitin, K. V.; Grandi, R.;
Libertini, E.; Pagnoni, U. M.; Schenetti, L. Tetrahedron
2003, 59, 1147.
19) De Buyck, L.; Bellesia, F.; Ghelfi, F.; Merighi, G.; Mucci,
A.; Pagnoni, U. M.; Pinetti, A.; Parsons, A. F. artricle in
preparation. See: Atti del XXI Congresso Nazionale della
Società Chimica Italiana; Società Chimica Italiana: Torino,
+
(
M – 29).
Anal. Calcd for C H Cl O: C, 53.34; H, 8.06. Found: C, 53.5; H,
10
18
2
8
.0.
Acknowledgment
We thank Dr. Fabrizio Roncaglia for the useful suggestions, the Mi-
nistero della Università e della Ricerca Scientifica e Tecnologica
2
003, Vol. 2, OR–CP-053.
20) Dow Chemical Co., Jpn. Kokai Tokkyo Koho, JP 58172337,
983; Chem. Abstr. 1984, 100, 67841.
(
(
MURST) and the Belgian N.F.W.O. and I.W.T. for financial assi-
1
stance.
(
(
21) Pews, R. G.; Lysenko, Z. Synth. Commun. 1985, 15, 977.
22) Bellesia, F.; De Buyck, L.; Ghelfi, F.; Libertini, E.; Pagnoni,
U. M.; Roncaglia, F. Tetrahedron 2000, 55, 7507.
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Synthesis 2003, No. 14, 2173–2178 © Thieme Stuttgart · New York