Novel bismethanofullerenes and ethenofullerene from the reaction of propiolates with C-60 in the presence of triphenylphosphine

Methyl propiolate reacts with C-60 in the presence of triphenylphosphine in toluene to give a bismethanofullerene 2. Compound 2 is an adduct of two methyl propiolate units to a C-60 moiety and consists of two methane bridges across two 6,6-ring junctions of the same six-membered ring on the fulleren...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 63; no. 18; pp. 6119 - 6122
Main Authors Hsiao, TY, Chidambareswaran, SK, Cheng, CH
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 04.09.1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FULLERENES
FUNCTIONALIZATION
CYCLOADDITION
BUCKMINSTERFULLERENE C-60
NMR
FULLERENE
C-13 ASSIGNMENTS
BUTA-2,3-DIENOATES
DERIVATIVES
MULTIPLE
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Summary:Methyl propiolate reacts with C-60 in the presence of triphenylphosphine in toluene to give a bismethanofullerene 2. Compound 2 is an adduct of two methyl propiolate units to a C-60 moiety and consists of two methane bridges across two 6,6-ring junctions of the same six-membered ring on the fullerene moiety. Similarly, ethyl propiolate reacts with C60 in the presence of PPh3 to yield bismethanofullerene 3. Detailed analysis of the products from the reaction of methyl propiolate with C-60 shows, in addition to 2 and C-60, an ethenofullerene 4 and an unidentified insoluble material were isolated. Compound 4, which may be viewed as a [2 + 2] cycloaddition adduct of C-60 and methyl propiolate, consists of a cyclobutene ring fused to the carbons on a 6,6-ring junction of the C-60 moiety. On the basis of the known chemistry of phosphine with electron-withdrawing alkynes and C-60, mechanisms are proposed to account for the formation of the bismethanofullerenes 2 and 3 and ethenofullerene 4.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo972344m