TY - JOUR
T1 - Diindenopyrenes
T2 - Extended 1,6- and 1,8-Pyrenoquinodimethanes with Singlet Diradical Characters
AU - Hibi, Daijiro
AU - Kitabayashi, Kenichi
AU - Fujita, Kazuya
AU - Takeda, Takashi
AU - Tobe, Yoshito
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/5/6
Y1 - 2016/5/6
N2 - Diindenopyrene 4b and its diastereomer, which are extended homologues of 1,6- and 1,8-pyrenoquinodimethanes fused by indene units, respectively, were synthesized by reaction of 1,4,5,8-tetrakis(mesitylethynyl)naphthalene (7) with bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate via cationic cyclization mechanisms at both centers of reaction. Unexpectedly, reaction of 7 with iodine, a reagent that typically gives products of cationic cyclization, gave cycloheptapentalenoindenophenalene derivative 9b and its diastereomer incorporating an azulene unit at one end of the - framework, via two different modes (radical and cationic) of cyclization at each reaction site. The physical properties of the products are presented, and the dual modes of cyclization of 7 and its model compound with only one reaction center are discussed.
AB - Diindenopyrene 4b and its diastereomer, which are extended homologues of 1,6- and 1,8-pyrenoquinodimethanes fused by indene units, respectively, were synthesized by reaction of 1,4,5,8-tetrakis(mesitylethynyl)naphthalene (7) with bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate via cationic cyclization mechanisms at both centers of reaction. Unexpectedly, reaction of 7 with iodine, a reagent that typically gives products of cationic cyclization, gave cycloheptapentalenoindenophenalene derivative 9b and its diastereomer incorporating an azulene unit at one end of the - framework, via two different modes (radical and cationic) of cyclization at each reaction site. The physical properties of the products are presented, and the dual modes of cyclization of 7 and its model compound with only one reaction center are discussed.
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U2 - 10.1021/acs.joc.6b00389
DO - 10.1021/acs.joc.6b00389
M3 - Article
AN - SCOPUS:84968862692
VL - 81
SP - 3735
EP - 3743
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 9
ER -