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At Last, 1,10‐Phenanthroline‐ N , N ′‐dioxide, A New Type of Helicene, has been Synthesized using HOF⋅CH 3 CN
Author(s) -
Rozen Shlomo,
Dayan Sharon
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19991203)38:23<3471::aid-anie3471>3.0.co;2-o
Subject(s) - helicene , phenanthroline , oxygen , chemistry , planar , materials science , crystallography , molecule , organic chemistry , computer science , computer graphics (images)
For more than 50 years the synthesis of 1,10‐phenanthroline‐ N , N ′‐dioxide ( 2 ) has been sought. The reason for the failure of all the earlier attempts is that the limited space in the bay area of the starting material 1,10‐phenanthroline ( 1 ) cannot accommodate two oxygen atoms. The oxidation has now been achieved with the oxygen‐transfer agent HOF⋅CH 3 CN, and X‐ray studies have revealed that the product is not planar but is a new type of helicene—in this way the “space problem” for the two oxygen atoms has been solved.