Donghong Yin et al.
UPDATES
0.32 mmꢁ0.25 mm), nitrogen as a carrier gas, injector temper-
ature 2208C, detector temperature 2008C, oven temperature
1508C, using trans-naphthane as an internal standard. The re-
tention times were: acrolein 2.58 min, myrcene 3.35 min,
ꢀmetaꢁ-myrac aldehyde 12.61 min, and ꢀparaꢁ-myrac aldehyde
13.89 min, respectively. After distillation and purification of
the upper clear liquid under vacuum, the product ꢀparaꢁ-myrac
aldehyde (bp 136–1388C/500 Pa) was identified by GC-MS,
[2] M. A. Sprecker, J. M. Sanders, W. L. Schreiber, H. Wat-
kins, J. F. Vinals, E. J. Shuster, T. J. OꢁRourke, M. L. Hage-
dorn, P. Klemarczyk, US Patent 4,250,338, 1981; US Patent
4,250,388, 1981.
[3] a) D. Yin, D. L. Yin, Z. Fu, Q. Li, J. Mol. Catal. A 1999,
148, 87–95; b) J. F. Liu, D. H. Yin, D. L.Yin, Z. H. Fu,
Q. H. Li, G. X. Lu, J. Mol. Catal. A 2004, 209, 171–177.
[4] a) T. Maruyama, H. Yamamura, T. Kotani, N. Kamiya, M.
Goto, Org. Biomol. Chem. 2004, 2, 1239–1244; b) N.
Gathergood, M. T. Garcia, P. J. Scammells, Green Chem.
2004, 6, 166–175; c) G. Y. Zhao, T. Jiang, H. X. Gao,
B. X. Han, J. Huang, D. H. Sun, Green Chem. 2004, 6,
75–77; d) R. C. Morales, V. Tambyrajah, P. R. Jenkins,
D. L. Davies, A. P. Abbott, Chem. Commun. 2004, 2,
158–159; e) S. Doherty, P. Goodrich, C. Hardacre, H. K.
Luo, D. W. Rooney, K. R. Seddon, P. Styring, Green
Chem. 2004, 6, 63–67; f) C. E. Song, W. H. Shim, E. J.
Roh, S-g Lee, J. H. Choi, Chem. Commun.2001, 12,
1122–1123; g) F. Zulfiqar, T. Kitazume, Green Chem.
2000, 2, 137–139.
[5] a) T. Fischer, A. Sethi, T. Welton, J. Woolf, Tetrahedron
Lett. 1999, 40, 793–796; b) M. J. Earle, P. B. McCormac
and K. R. Seddon, Green Chem. 1999, 1, 23–25; c) J. S.
Yadav, B. V. S. Reddy, J. S. S. Reddy, R. S. Rao, Tetrahe-
dron. 2003, 59, 1599–1604; d) J. K. Park, P. Sreekanth,
B. M. Kim, Adv. Synth. Catal. 2004, 346, 49–52.
[6] a) A. Kumar, S. S. Pawar, J. Mol. Catal. A 2004, 208, 33–
37; b) C. W. Lee, Tetrahedron Lett. 1999, 40, 2461–2464;
c) I. Meracz, T. Oh, Tetrahedron Lett. 2003, 44, 6465–
6468.
1
FT-IR (Nicolet Nexus FT-IR Spectrometer), H NMR and
13C NMR (INOVA-400-Varian) spectra, the data of which
were in good agreement with those of aþn authentic samplþe;
MS: m/z¼192 [Mþ peak], 177 [192 CH3] , 149 [177 CHO] ,
ꢀ
ꢀ
þ
þ
ꢀ
¼
ꢀ
[122 CHO] ,þ 69
þ
122
[192 CH2CH CHO] ,
93
þ
¼
¼
ꢀ
ꢀ
[(CH3)2 CHCH2] , 41 [CH2 CH CH2] , 29 [ CHO] ; IR:
n¼2820, 2720, 1730, 1390,1370, 1205, 805 cmꢀ1
;
1H NMR
(400 MHz, CDCl3): d¼1.60, 1.68 [2 s, 6 H (CH3)2], 1.92–2.10
ꢀ
ꢀ ꢀ
ꢀ
ꢀ ꢀ
ꢀ
¼
ꢀ
(m, CH2 CH2 CH2
,
,
CH2 ), 2.23 (m, CH CH2), 2.46
ꢀ
ꢀ
¼
ꢀ
¼
ꢀ
(m, CH ), 5.08 [m, CH C(CH3)2], 5.43 (m, CH CH2),
9.69 (s, CHO); 13C NMR (100 MHz, CDCl3): dC ¼17.66
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
( CH3), 22.53 ( CH3), 24.48 ( CH2), 25.68 ( CH2), 26.30
ꢀ
ꢀ
ꢀ
ꢀ
( CH2), 26.86 ( CH2), 37.58 ( CH2), 46.07 ( CH), 118.34
¼
¼
¼
¼
( CH), 124.04 ( CH), 131.57 ( C), 138.01 ( C), 204.82
ꢀ
( CHO).
Acknowledgements
The project was sponsored by the Scientific Research Founda-
tion for the Returned Overseas Chinese Scholars, Ministry of
Education [2001-498]. The authors also thank the Natural Sci-
ence Foundation of Hunan Province for financial support to
this project (01JJY3008).
[7] a) A. P. Abbott, G. Capper, D. L. Davies, H. L. Munro,
R. K. Rasheed, V. Tambyrajah, Chem. Commun. 2001,
19, 2010–2011; b) A. P. Abbott, G. Capper, D. L. Davies,
R. K. Rasheed, V. Tambyrajah, Green Chem. 2002, 4,
24–26.
References
[1] a) M. Anzaldi, E. Sottofattori, F. Dusatti, M. Ferro, M.
Pani, A. Balbi, Eur. J. Med. Chem. 2000, 35, 797–803;
b) A. Molinari, A. Oliva, P. Reinoso, J. M. M. del Corral,
M. A. Castro, M. Gordaliza, M. P. Gupta, P. Sols, A. San
Feliciano, Eur. J. Med. Chem. 2002, 37, 177–182; c) V. V.
Veselovsky, A. S. Gybin, A. V. Lozanova, A. M. Moiseen-
kov, W. A. Smit, R. Caple, Tetrahedron Lett. 1988, 29,
175–178.
[8] R. Sheldon, Chem. Commun. 2001, 23, 2399–2407.
[9] a) J. G. Huddleston, H. D. Willauer, R. P. Swatloski, A. E.
Visser, R. D. Rogers, Chem. Commun. 1998, 16, 1765–
ˆ
1766; b) P. Bonhote, A-P. Dias, N. Papageorgiou, K. Ka-
lyanasundaram, M. Grꢃtzel, Inorg. Chem. 1996, 35,
1168–1178; c) J. S. Wilkes, J. A. Levisky, R. A. Wilson,
C. L. Hussey, Inorg. Chem. 1982, 21, 1263–1265; d) A. Ka-
mal, G. Chouhan, Adv. Synth. Catal.2004, 346, 579–582.
142
ꢂ 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
Adv. Synth. Catal. 2005, 347, 137–142