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 Radical
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Specialty Chemical home >
Radical reaction
Recently radical reaction is reported as useful
bond-making method in organic synthesis. Wako has been developing
various azo initiators and is working on process development of
organic synthesis utilizing unique initiators. We will offer efficient
and stereoselective reaction picking suitable radical initiators
for reaction system.
Click here for further information of V-70.(V-70)
Click here for other azo initiators.(water-soluble)(oil-soluble)
radical reaction utilized V-70(1)
| Entry |
Initiator |
Time(hr) |
Yield(%)of 3a |
| 1 |
AIBN |
24 |
No Reaction |
| 2 |
BPO |
24 |
No Reaction |
| 3 |
Et3B |
18 |
44 |
| 4 |
hv |
6 |
85 |
| 5 |
V-70 |
12 |
89 |
Use of V-70 as radical initiator that has activity of initiator
in low temperature can proceed reaction utilized unstable bromomalononitrile.
stereoselective cyclization utilized V-70(2)
| Entry |
Initiator |
Solvent |
Temp. (°C) |
Yield (%) |
Ratio (anti:syn) |
| 1 |
hv |
CH2Cl2 |
refl. |
86 |
94:6 |
| 2 |
Et3B |
CH2Cl2 |
-78 |
69 |
99:1 |
| 3 |
AIBN |
C6H6 |
refl. |
80 |
86:14 |
| 4 |
V-70L |
CH2Cl2 |
r.t. |
85 |
98:2 |
The table shows effect of various radical initiators under
intramolecular cyclization with the use of 2-bromopentenate. In
use of V-70L products are obtained in excellent yield and stereoselectivity.
Reference
- Y. Kita, A. Sano, T. Yamaguchi, M. Oka, K. Gotanda, M. Matsugi,Tetrahedron Lett., 38, 3549 (1997)
- M. Matsugi, K. Gotanda, C. Ohira, M. Suemura, A. Sano, Y. Kita,J. Org. Chem., 64, 6928 (1999)
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Outline
of custom manufacturing (custom synthesis)