Adduct of C[sub 70] at the equatorial belt. Photochemical cycloaddition with disilirane

Journal Article · Wed Mar 23 04:00:00 EST 1994 · Journal of the American Chemical Society; (United States)

DOI:https://doi.org/10.1021/ja00085a056· OSTI ID:7267151

Akasaka, Takeshi; Mitsuhida, Eiko; Ando, Wataru ^[1]; Kobayashi, Kaoru; Nagase, Shigeru ^[2]

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1. Univ. of Tsukuba, Ibaraki (Japan)
2. Yokohama National Univ. (Japan)

We report the novel photochemical reaction of C[sub 70] with a disilirane affording a cycloadduct as the first silylated C[sub 70]. This is the first example in which addition occurs at the equatorial belt (e-e bond). A toluene solution of C[sub 70] (3.3 x 10[sup [minus]3] M) and 1,1,2,2-tetramesityl-1,2-disilirane (1, 3.3 x 10[sup [minus]3] M) was photolyzed with a high-pressure mercury-arc lamp (cutoff < 300 nm) to afford a thermally stable 1:1 adduct (2) with complete consumption of C[sub 70]. Adduct 2 can be isolated readily in 85% yield by preparative HPLC. No thermal cycloaddition occurs at elevated temperatures up to 100[degree]C. FAB mass spectrometry of 2 (C[sub 107]H[sub 46]Si[sub 2]) displays a peak for 2 at 1390-1386 as well as one for C[sub 70] at 843-840 which arises from loss of 1. The UV-vis absorption spectrum of 2 is virtually identical to that of C[sub 70] except for subtle differences in the 350-550 nm region. 2 exhibits a new band at 407 nm but lacks the C[sub 70] bands at 381 and 471 nm. 24 refs., 3 figs., 1 tab.

• OSTI ID: 7267151
• Journal Information: Journal of the American Chemical Society; (United States), Journal Name: Journal of the American Chemical Society; (United States) Vol. 116:6; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400102 -- Chemical &amp; Spectral Procedures
400201 -- Chemical &amp; Physicochemical Properties
400500* -- Photochemistry
ADDUCTS
ALKYLATED AROMATICS
AROMATICS
CARBON
CHEMICAL BONDS
CHEMICAL REACTIONS
CHROMATOGRAPHY
DECOMPOSITION
DERIVATIZATION
ELEMENTS
FULLERENES
HYDROCARBONS
MAGNETIC RESONANCE
MASS SPECTROSCOPY
NONMETALS
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
PHOTOCHEMICAL REACTIONS
PHOTOLYSIS
RESONANCE
SEPARATION PROCESSES
SILICON COMPOUNDS
SPECTRA
SPECTROSCOPY
TOLUENE
ULTRAVIOLET SPECTRA