Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
28.1.2.6.2 Applications of 2,3,5,6-Tetrahalobenzo-1,4-quinones in Organic Synthesis

DOI: 10.1055/sos-SD-028-00020

Balci, M.; Çelik, M.; Gültekin, M. S.Science of Synthesis, (20062849.

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]

Meeeee 88 Meeeeeeee ee Meeeeeeeeee Meeeeeeee ee eee Meeeeeeeeeeeee ee e-Meeeeeeee[‌88‌]

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[‌88‌,‌88‌‌88‌]

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]

e Meeee eee eeeeeeee.

References


Cookie-Einstellungen