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Ward, J. Am. Chem. Soc., 94, 552 (1972). (11) The carboxyl inversion product (4b) is formed in 18% yield but does not exhibit CIDNP in either the 1 *H or ,3C NMR. This supports a nonradical mechanism for formation of this product. Furthermore, 4b is stable under the reaction conditions and is thus not a precursor of 3b or 5-7. The relative yields of 3b and 5-7 are also insensitive to the concentration of 1b (0.045-0.5 M) and to the addition of excess m-chlorobenzoic acid (saturated in ODCB at 0.2 M). This makes it unlikely that either induced decomposition or acid promoted ionization of 1b contribute significantly to the reaction under these conditions. (12) (a)

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The mass spectra of l-(trimethylsilyl)-3-phenylpropane and /3-(trimethylsilyl)styrene have been studied in detail. The mass spectral rearrangements observed are shown to occur by interaction of the silyl center and the phenyl ring.Mass spectroscopy is a particularly powerful analyti-

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Volatile trimethylsilyl derivatives have been a popular choice for vapor phase chromatographic separation of nonvolatile materials. This has led to extensive study of the mass spectra of these derivatives for alcohols,1•2 carboxylic acids,3 and other functional groups.4The mass spectra of functionalized organosilicon compounds per se have only been slightly examined.6 We have observed in the mass spectrum of methyl 4-tri-methylsilylbutyrate6 two novel intramolecular rearrangements involving the silyl center.