Tetrahedron

Wolff rearrangement of (1-diazo-2-oxoalkyl) silanes

R Brückmann, K Schneider, G Maas

Index: Brueckmann, Ralf; Schneider, Klaus; Maas, Gerhardt Tetrahedron, 1989 , vol. 45, # 17 p. 5517 - 5530

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Citation Number: 34

Abstract

Photochemical decomposition of (1-diazo-2-oxoalkyl) silanes 6a-1 results in Wolff rearrangement yielding silyl ketenes 8a-1. From (1-diazo-3, 3-dimethyl-2-oxobutyl) silanes 6c-f, 2-silyl-cyclobutanones 9c-f are formed as by-products, arising from intramolecular C/H insertion of the acyl carbene intermediate. Irradiation of diazo-triisopropylsilyl-acetamide 6m yields only β-lactam 16 and γ-lactam 17. Wolff rearrangement also takes place on copper ...