Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Chemistry of Silyl Diazo Compounds
Akira SEKIGUCHIWataru ANDO
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1977 Volume 35 Issue 11 Pages 897-908

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Abstract
The chemistry of silyl diazo compounds is reviewed. Silyl diazo compounds are more stable than the corresponding carbon diazo compounds due to the pΠ-dΠ resonance. Silyl diazo compounds react th a variety of reagents such as electron deficient olefins, nitriles, acids, halogen etc. Silylcarbenes generated by the decomposition of silyl diazo compounds are found to be electrophilic by the reactions with olefins and compounds containing hetero atom. The reactions of silylcarbenes with olefin give stereospecific addition products and with sulfides, ethers, and alkyl halides form the corresponding ylides. The intramolecular reactions of silylcarbenes are also described. It is found that singlet silylcarbenes can produce silaethenes which are species having a silicon-carbon double bond.
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© The Society of Syhthetic Organic Chemistry, Japan
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