At Last, 1,10-Phenanthroline-N,N′-dioxide, A New Type of Helicene, has been Synthesized using HOF⋅CH3CN
- 30 November 1999
- journal article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 38 (23) , 3471-3473
- https://doi.org/10.1002/(sici)1521-3773(19991203)38:23<3471::aid-anie3471>3.0.co;2-o
Abstract
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⋅CH3CN, 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.Keywords
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