| Abstract
| - A novel migration of the trimethylsilyl group during reaction of methoxy[(trimethylsilyl)ethoxy]carbene with N-phenylmaleimide (NPM) and with C60, reported earlier, was examined by meansof deuterium labeling of the carbene. For the NPM case it was found that the CD2CH2SiMe3 group,initially bound to oxygen, became the CH2CD2SiMe3 group bound to carbon in the end product.Not only had the trimethylsilylethyl group moved from oxygen to carbon, but the TMS group hadalso migrated 1,2 along the ethyl chain. For the C60 case, complete scrambling of the CD2 groupwas observed, strongly implying the involvement of a silacyclopropane carbocation responsible forproduct formation. The labeling study supports the mechanism that was tentatively advanced earlierfor addition to NPM and one of the possibilities suggested for addition to C60.
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