7920
J. Auge´, R. Gil / Tetrahedron Letters 43 (2002) 7919–7920
Table 1. Cyclotrimerization of aldehydes under solvent-free conditions at room temperature
Entry
Aldehyde
TMSCl (equiv.)
Work-up
Yield (%)
Mp (°C)
1
2
3
4
5
6
7
8
Me(CH2)6CHO
Me2CHCHO
C6H11CHO
0.004
0.004
0.004
0.004
0.004
0.01
A
A
A
A
A
B
87
72
89
81
45
64
78
70
34
53–54
195
69
41
Me3CCHO
Me(CH2)8CHO
Ph(CH2)2CHO
MeCH2CHO
MeCHO
62–63
0.004
0.004
C
C
Condition A: recrystallization from ethanol. Condition B: silica gel chromatography with cyclohexane/ethyl acetate as the eluent. Condition C:
direct evaporation of the reaction mixture.
In summary, our protocol provides a convenient prepa-
ration of 1,3,5-trioxanes from aldehydes. The small
amount of the catalyst, its easy accessibility and
removal, the absence of solvent, along with the mild
conditions, are the main advantages of the process.
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10. Chandrasekhar, S.; Takhi, M.; Ravindra Reddy, Y.;
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