871507-71-0Relevant academic research and scientific papers
Synthesis and property of novel phthalocyanine having a 3,5-bis-pentafluorosulfanylphenyl group on the ?±-peripheral position
Iida, Norihito,Tokunaga, Etsuko,Saito, Norimichi,Shibata, Norio
, p. 93 - 98 (2014)
The pentafluorosulfanyl (SF5) group is bulky, highly lipophilic, highly electronegative, and highly stable. Despite the potential use of SF5-containing phthalocyanines, no example exists. We herein report the synthesis of 3,5-bis-pentafluorosulfanylphenyl ((SF5)2Ph)-substituted phthalocyanine onto the ?±-peripheral position for the first time. Regioselective synthesis was possible by the effect of the SF5 moiety via macrocyclization. The synthesis of phthalocyanines with CF3 and H instead of SF5 was also carried out in order to investigate the effect of SF5. Phthalocyanines were compared using UV/Vis spectra. Phthalocyanine with SF5 exists free from aggregation and protonation in dichloromethane solution. The two planes of 3,5-(SF5)2Ph and parent Pc ring in space are nearly perpendicular at which they meet is a right angle, while the two planes of CF3 analogue in space are not.
3,5-Bis(pentafluorosulfanyl)phenylboronic acid: A new organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes
Yang, Yu-Dong,Lu, Xu,Tokunaga, Etsuko,Shibata, Norio
, p. 204 - 209,6 (2020/07/31)
3,5-Bis(pentafluorosulfanyl)phenylboronic acid 1 was introduced as an efficient organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes. A variety of 2-alkynic 1,3-dicarbonyl compounds were smoothly converted to ene-carbocyclization products in moderate to excellent yields. Compared with the reported catalyst, 3-nitro phenylboronic acid, catalyst 1 is slightly better in a non-polar solvent such as toluene and Solkane365mfc (1,1,1,3,3-pentafluorobutane). These results indicate that the SF5 function can be a lipophilic and sterically demanding alternative to the NO2 group in catalyst design.
