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Photochemical Reaction of o ‐Phthalaldehyde with Fullerene C 60 : The Stimulus for the Phthalide Additions to C 60
Author(s) -
Tzirakis Manolis D.,
Malliaros Nikitas G.,
Orfanopoulos Michael
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901363
Subject(s) - phthalide , chemistry , photochemistry , reactivity (psychology) , tetrathiafulvalene , o phthalaldehyde , yield (engineering) , organic chemistry , molecule , medicine , materials science , alternative medicine , high performance liquid chromatography , pathology , metallurgy , derivatization
A new, simple, and rapid photochemical reaction of o ‐phthalaldehyde with C 60 has been disclosed. This reaction afforded exclusively the unanticipated C 60 ‐phthalide derivative 11 in good yield. The formation of this product is consistent with the intervention of a key free‐radical intermediate –a benzylic radical– in the course of the reaction. The structure of 11 has been determined by the combined use of experimental and theoretical NMR studies. In the course of this study we further disclosed a new mode of radical reactivity of C 60 with a series of substituted phthalides ( 2 , 15 – 17 ) catalyzed by tetrabutylammonium decatungstate.