Reaction of C60 with Dimethyldioxirane—Formation of an Epoxide and a 1,3‐Dioxolane Derivative

Yiannis Elemes; Scott K. Silverman; Chimin Sheu; Michelle Kao; Christopher S. Foote; Marcos M. Alvarez; Robert L. Whetten

doi:10.1002/anie.199203511

Reaction of C₆₀ with Dimethyldioxirane—Formation of an Epoxide and a 1,3‐Dioxolane Derivative

Yiannis Elemes, Scott K. Silverman, Chimin Sheu, Michelle Kao, Christopher S. Foote, Marcos M. Alvarez, Robert L. Whetten

Research output: Contribution to journal › Article › peer-review

194 Scopus citations

Abstract

Not an oxygen‐bridged annulene (structural type 1) but rather an epoxide (structural type 2) is the product of the reaction of dimethyldioxirane with C₆₀. 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. (Figure Presented.)

Original language	English (US)
Pages (from-to)	351-353
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	31
Issue number	3
DOIs	https://doi.org/10.1002/anie.199203511
State	Published - Mar 1992
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry

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title = "Reaction of C60 with Dimethyldioxirane—Formation of an Epoxide and a 1,3‐Dioxolane Derivative",

abstract = "Not an oxygen‐bridged annulene (structural type 1) but rather an epoxide (structural type 2) is the product of the reaction of dimethyldioxirane with C60. 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. (Figure Presented.)",

author = "Yiannis Elemes and Silverman, \{Scott K.\} and Chimin Sheu and Michelle Kao and Foote, \{Christopher S.\} and Alvarez, \{Marcos M.\} and Whetten, \{Robert L.\}",

year = "1992",

month = mar,

doi = "10.1002/anie.199203511",

language = "English (US)",

volume = "31",

pages = "351--353",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

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T1 - Reaction of C60 with Dimethyldioxirane—Formation of an Epoxide and a 1,3‐Dioxolane Derivative

AU - Elemes, Yiannis

AU - Silverman, Scott K.

AU - Sheu, Chimin

AU - Kao, Michelle

AU - Foote, Christopher S.

AU - Alvarez, Marcos M.

AU - Whetten, Robert L.

PY - 1992/3

Y1 - 1992/3

N2 - Not an oxygen‐bridged annulene (structural type 1) but rather an epoxide (structural type 2) is the product of the reaction of dimethyldioxirane with C60. 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. (Figure Presented.)

AB - Not an oxygen‐bridged annulene (structural type 1) but rather an epoxide (structural type 2) is the product of the reaction of dimethyldioxirane with C60. 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. (Figure Presented.)

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 3

ER -

Reaction of C₆₀ with Dimethyldioxirane—Formation of an Epoxide and a 1,3‐Dioxolane Derivative

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