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Reaction of C 60 with Dimethyldioxirane—Formation of an Epoxide and a 1,3‐Dioxolane Derivative
Author(s) -
Elemes Yiannis,
Silverman Scott K.,
Sheu Chimin,
Kao Michelle,
Foote Christopher S.,
Alvarez Marcos M.,
Whetten Robert L.
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199203511
Subject(s) - dimethyldioxirane , epoxide , dioxolane , diradical , chemistry , acetone , derivative (finance) , photochemistry , stereochemistry , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis , physics , nuclear physics , singlet state , financial economics , economics , excited state
Not an oxygen‐bridged annulene (structural type 1 ) but rather an epoxide (structural type 2 ) is the product of the reaction of dimethyldioxirane with C 60 . In a competing reaction, a 1,3‐dioxolane (structural type 3 ) is formed—probably by a diradical mechanism. Cleavage of acetone from 3 leading to 2 was not observed at temperatures up to 110°C. Compound 3 could provide access to ring‐opened fullerenes.