meso-Tetraarylporphyrins as dipolarophiles in 1,3-dipolar cycloaddition reactions

Abstract

meso-Tetraarylporphyrins participate, as dipolarophiles, in 1,3-dipolar cycloaddition reactions with azomethine ylides to yield novel chlorins and isobacteriochlorins.

Cycloreversion and other gas‐phase reactions of neutral and cationic pyrrolidine‐fused chlorins and isobacteriochlorins under ion bombardment and electrospray

“…1), were synthesized via 1,3-dipolar cycloaddition reactions. 20 Liquid secondary ion mass spectrometry (LSIMS) and electrospray ionization mass spectrometry (ESI-MS) were used to investigate their gas-phase behavior which presents interesting and unusual features. …”

Observation of phenyl-fused porphyrinoids during the ESI mass spectrometric analysis of meso-pentafluorophenyl-substituted porphyrin and corrole

“…Further, the pentafluorophenyl groups mediate the solubility of porphyrins in fluorinated solvents and supercritical CO 2 [22,23]. Lastly, 19 F is NMR active, and the pentafluorophenyl group offers a convenient NMR tag to elucidate the structure of complex porphyrinic derivatives [3,24].…”

“…Their popularity as, for instance, model compounds for naturally occurring cofactors arises from their straightforward syntheses and the option to widely vary the type of substituents on the aryl rings [1]. One particular mesoaryl group, the electron-withdrawing pentafluorophenyl group, is commonly utilized when chemical inertness is to be imparted onto the porphyrinic macrocycle, such as increased stability toward oxidative degradation [2][3][4][5][6]. Metalloporphyrins and metallocorroles (based on the ligand meso-tris(pentafluorophenyl)corrole, T F PC) used in group transfer catalyses also take advantage of the stabilizing effects of the pentafluorophenyl moiety [5][6][7].…”

Synthesis of Metallo-Deuteroporphyrin Derivatives and the Study of Their Biomimetic Catalytic Properties

“…The introduction of electron-withdrawing substituents on the porphyrin periphery, especially halogenated and perhalogenated phenyl porphyrins, has proved very successful in creating robust catalysts (Traylor et al, 1991). Steric protection of the mesoposition of the porphyrin has also been used effectively (Silva et al, 1999). In practice, however, these are not entirely separate approaches, because almost all of the electronwithdrawing substituents will also contribute significant steric protection to the metalloporphyrin (Suslick, 2000).…”