Abstrakt: |
The reaction of 6-(2,3,3-trifluorocyclobutenyl)-4,5-diazaspiro[2.4]hept-4-ene with NaOMe in MeOH results in a mixture of isomeric (6E)- and (6Z)-6-(2-fluoro-3,3-dimethoxycyclobutylidene)-4,5-diazaspiro[2.4]hept-4-ene due to the formal substitution of methoxy groups for two geminal fluorine atoms. Both of the isomers selectively add acetyl chloride at the azo-olefin unit to give 4-acetyl-6-(1-chloro-2-fluoro-3,3-dimethoxycyclobutyl)-4,5-diazaspiro[2.4]hept-4-ene as the trans-isomer in greater than 95% yield. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2003) |