Insertion of Fischer Carbene Complexes into the Carbon-Carbon Bond of 1,2-Diphenylcyclopropenone: Formation of Cyclobutenones and o- and p-Methoxyphenol Derivatives

Date

1994-08-01

Author

Zora, Metin

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Thereactionbetween1,2-diphenylcyclopro-penoneandFischercarbenecomplexeshasbeeninves-tigated.Thereactionproducedamixtureofdipheny-lacetyleneandcyclobutenones.Whena,ß-unsaturatedcarbenecomplexeswereemployed,benzannulationprod-uctsanddiphenylacetylenewereproduced.Amecha-nisminvolvingmetallacyclobutenoneformation,followedbyeithercarbeneinsertionandreductiveeliminationorfragmentationhasbeenproposed.Recently,wereportedthatcarbon—carbonbondin-sertionisthemajorreactionpathwaywhenFischercarbenecomplexesreactwith1,2-cyclobutenediones,1affording4-cyclopentene-l,3-dionesand/or5-alkylidene-furanones.Otherstrainedringsmightleadtoinsertionproductsaswell.Avarietyofadditionalringsystemsweretestedinthisreaction,includingcyclobutenones,cyclobutenes,cyclopropanes,cyclopentadienones,andcyclopropenones.Ofthese,onlythecyclopropenoneringsystemaffordedcarbon—carbonbondinsertionproductswhentreatedwithFischercarbenecomplexes.Hereinwereportthereactionbetween1,2-diphenylcyclopro-penoneandFishercarbenecomplexes.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry

URI

https://hdl.handle.net/11511/36332

Journal

Organometallics

DOI

https://doi.org/10.1021/om00020a059

Collections

Department of Chemistry, Article

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Citation Formats

M. Zora, “Insertion of Fischer Carbene Complexes into the Carbon-Carbon Bond of 1,2-Diphenylcyclopropenone: Formation of Cyclobutenones and o- and p-Methoxyphenol Derivatives,” Organometallics, pp. 3370–3373, 1994, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/36332.