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Claisen Rearrangement of Graphite Oxide: A Route to Covalently Functionalized Graphenes
Author(s) -
Collins William R.,
Lewandowski Wiktor,
Schmois Ezequiel,
Walish Joseph,
Swager Timothy M.
Publication year - 2011
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/anie.201101371
Subject(s) - claisen rearrangement , graphite oxide , graphene , oxide , chemistry , sigmatropic reaction , aqueous solution , saponification , epoxide , graphite , organic chemistry , covalent bond , carboxylic acid , polymer chemistry , materials science , nanotechnology , catalysis
On the GO : The basal plane allylic alcohol functionality of graphite oxide (GO) can be converted into N , N ‐dimethylamide groups through an Eschenmoser–Claisen sigmatropic rearrangement by using N , N ‐dimethylacetamide dimethyl acetal. Subsequent saponification of these groups affords the carboxylic acids (see picture), which, when deprotonated, electrostatically stabilize the graphene sheets in an aqueous environment.