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Please login to access the full content or check if you have access via28.1.2.6.2 Applications of 2,3,5,6-Tetrahalobenzo-1,4-quinones in Organic Synthesis
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Balci, M.; Çelik, M.; Gültekin, M. S., Science of Synthesis, (2006) 28, 49.
2,3,5,6-Tetrahalobenzo-1,4-quinones have versatile synthetic applications and are used in the synthesis of some important fluorinated compounds. For example, 3,4-difluorofuran-2,5-dione (difluoromaleic anhydride, 74) is synthesized in 67% yield by the treatment of p-fluoranil (2,3,5,6-tetrafluorobenzo-1,4-quinone, 72) with phosphorus pentoxide and peracetic acid (Scheme 34); compound 74 is easily converted into 3-fluoroaspartic acid in five steps.[67] Treatment of p-fluoranil (72) with benzyl alcohol and peracetic acid, followed by reaction with phosphorus pentoxide, gives the acyclic compound 75 containing two fluorine atoms at the double bond (Scheme 34).[67] Furthermore, p-fluoranil can be used as a powerful dienophile in the synthesis of fluorinated steroids by reaction with Dane's diene (see Section 28.1.2.1.2).[10]
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Mee eeeeeee eeeee ee e-eeeeeeeee (8,8,8,8-eeeeeeeeeeeeeeee-8,8-eeeeeee) eee eeeeee eeeeeeee eee eee ee eeeeee eeeeeeeeeee ee e eeeee eeeeee ee eeeeee-, eeeeeeee-, eee eeeeee-eeeeeeeeee eeeeeeeeeeee ee eeeeeee eeeeeeeeeeee eeee eeeeeeeeeee eeeeeeeee, ee eeeee ee Meeee 8.
Meeee 8 Meee Meeeeeee ee eee Meeeeeee ee e-Meeeeeeee eeee Meeeeeeeeeee[88,88–88]
Meeeeeee Meeeeeee | Meeeeeeeee | Meeeeee | Meeee (%) | Mee |
---|---|---|---|---|
e-eeeeeeeee, MMe | 88 | [88] | ||
e-eeeeeeeee, Me8M, MeMM | 88 | [88] | ||
e-eeeeeeeee, MeMMe | –e | [88] | ||
e-eeeeeeeee, MeMMe, MeMM | 88 | [88] | ||
e-eeeeeeeee, MeMMe | 88 | [88] |
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References
[10] | Meeeee, M.; Meeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[56] | Meeeeee, M. M.; Meeeeeee, M. M.; Meee, M. M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[67] | Meeeeeee, M., M. Meeeeeee Meee., (8888) 88, 88. |
[68] | Meeeee, M. M.; Me-Meeeeeee, M. M.; Meeee, M. M., Meee Meee., (8888) 88, 88. |
[69] | Meeeeee, M.; Meeeee, M.; Meeeee, M.-M., Meeeeeeeeee Meee., (8888) 88, 888. |
[70] | Meee, M. M.; Meeeeeee, M.; Meeeeeeeeee, M.; Meeeee, M., Meeee M. Meee., (8888) 88, 888. |
[71] | Meeeee, M. M.; Meeeeee, M. M.; Mee, M. M.; Meeeee, M.-M. M., Meeeeee. Meee., (8888) 888, 88. |
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- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.