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Thermal Decomposition of α-Diazo-α-(trialkylsilyl)alkanones - Intramolecular C/H Insertion of Siloxyalkylidenecarbene Intermediates
Brueckmann, Ralf,Maas, Gerhard
, p. 635 - 642 (2007/10/02)
α-Diazo-α-(trialkylsilyl)alkanones 6 have been prepared by silylation of primary α-diazo ketones 4 with trialkylsilyl triflates 5.Diazo compounds 6 are decomposed in boiling benzene to give 1-oxa-2-sila-4-cyclopentenes 7 and 9.Evidence is presented that this transformation proceeds via alkylidenecarbenes 17 which undergo 1,5-cyclization by carbene insertion into a SiC-H bond.
