TY - JOUR
T1 - Effect of aryl substituents on intramolecular cyclization of 2,2′-biphenoquinones
AU - Hayashi, Naoto
AU - Kanda, Akifumi
AU - Kamoto, Taku
AU - Higuchi, Hiroyuki
AU - Akita, Takeyuki
PY - 2009
Y1 - 2009
N2 - Effect of aryl substituents on intramolecular cyclizations of 3,3′,5,5′-tetraaryl-2,2′-biphenoquinones (Ar = phenyl (la) and 4-methoxyphenyl (1b)) has been studied. In benzene, 1a gave 2,4,6,8-tetraphenyldibenzofuran-1-ol (10) gradually as a main product, indicating the phenyl substituents preferred to stabilize the intermediate by derealization of the negative charge rather than that of the positive one. In contrast, the reaction of 1b occurred spontaneously in order to give a complex mixture, which should be due to 4-methoxyphenyl substituent at the 3 position.
AB - Effect of aryl substituents on intramolecular cyclizations of 3,3′,5,5′-tetraaryl-2,2′-biphenoquinones (Ar = phenyl (la) and 4-methoxyphenyl (1b)) has been studied. In benzene, 1a gave 2,4,6,8-tetraphenyldibenzofuran-1-ol (10) gradually as a main product, indicating the phenyl substituents preferred to stabilize the intermediate by derealization of the negative charge rather than that of the positive one. In contrast, the reaction of 1b occurred spontaneously in order to give a complex mixture, which should be due to 4-methoxyphenyl substituent at the 3 position.
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U2 - 10.3987/COM-08-S(D)57
DO - 10.3987/COM-08-S(D)57
M3 - Article
AN - SCOPUS:67651100879
SN - 0385-5414
VL - 79
SP - 865
EP - 872
JO - Heterocycles
JF - Heterocycles
IS - C
ER -