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Reactivity of Carboxyl‐functionalized Cubane‐like Photocyclodimer of 2‐Substituted Naphthalene toward Aromatic Amines
Author(s) -
LIAO Guihong,
LUO Lin,
WU Xiaoling,
LEI Lei,
TUNG Chenho,
WU Lizhu
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990103
Subject(s) - chemistry , cubane , reactivity (psychology) , naphthalene , medicinal chemistry , stereochemistry , crystal structure , organic chemistry , medicine , alternative medicine , pathology
Reactions of carboxyl‐functionalized cubane‐like photocyclodimer 2 with a series of aromatic amines 3 were investigated for understanding the reactivity of this unique system. Spectroscopic and X‐ray crystal structural analyses demonstrate that N , N′ ‐dicyclohexylcarbodiimide (DCC) is reactive toward 2 affording stable 4 with a well‐retained cubane‐like structure. With the assistance of DCC, mono‐ and diacyl‐substituted photocyclodimers of 2‐sustituted naphthalene ( 5 and 6 ) have also been achieved in reasonable yields in addition to the formation of 4 . Subtle change in the electronic properties of the series of aromatic amines 3 modulates the reactivity and product distribution remarkably.