Acetylene Equivalent for Bay Region Diels-Alder Cycloaddition
- 21 October 2010
- journal article
- synthesis of-materials-and-unnatural-products
- Published by Georg Thieme Verlag KG in Synfacts
- Vol. 2010 (11) , 1244
- https://doi.org/10.1055/s-0030-1258731
Abstract
Nitroethylene is generated in situ by the dehydration of 2-nitroethanol with phthalic anhydride. This active dienophile usually gives thermally stable Diels-Alder adducts that do not lose the nitro group. However, when reacted with perylene (1), the bay region is converted into an unsubstituted benzene ring. Bisanthene 3, which is used as a model compound for the carbon nanotube bay regions, gives a double Diels-Alder cycloadduct in good yield.Keywords
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