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Migratory aptitude of substituents on silicon atoms of disilylcarbenes

✍ Scribed by Akira Oku; Toshiyuki Miki; Yasuyoshi Ose

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 291 KB
Volume: 9
Category: Article
ISSN: 0894-3230
DOI: 10.1002/(sici)1099-1395(199609)9:9<619::aid-poc822>3.0.co;2-w

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✦ Synopsis

Photolysis of (dimethylphenylsilyl)(trimethylsilyl)diazomethane in t-BuOH yielded three different t-BuOsubstituted (silylalkyl)silanes. The migratory aptitude of substituents from the silicon atoms to the carbenic center was found to be in the order Ph:Me (on phenyl-substituted Si):Me (on TMS)=3.8: 1.0: 1.0, the opposite of that reported for monosilylcarbenes. The photolysis of (1-phenyl-1-silacyclobutyl)(trimethylsilyl) diazomethane gave two silyl-substituted silacyclobutanes and one ring-expanded silacyclopentane. Again, the migratory aptitude of substituents was in the order Ph : ring-methylene : Me = 4.5 : 1.4: 1.0, showing that the ring shifts faster than Me and also Ph shifts faster than any alkyl substituent.

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