Some chemistry of 6,7-benzotricyclo[3.3.1.02,8]-nona-3,6-dien-9-one (benzobarbaralone)

A. Eisenstadt

doi:10.1016/S0040-4020(01)97103-0

Some chemistry of 6,7-benzotricyclo[3.3.1.0^2,8]-nona-3,6-dien-9-one (benzobarbaralone)

A. Eisenstadt

Tel Aviv University

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Some reactions of benzobarbaralone 3 have been studied. Ring expansion occurs in reaction of 3 with diazomethane-lithium chloride to yield benzobullvalone 5 and the spirooxirane 6. The tosylhydrazone of 5 was converted to the fluxional benzobullvalene 9. Decarbonylation of 3 to benzocyclooactatetraene occurs upon irradiation. On reaction with Fe₂CO)₉, 3 gives a σ-π allyl tricarbonyliron complex, 11, with rearranged skeleton.

Original language	English
Pages (from-to)	2353-2356
Number of pages	4
Journal	Tetrahedron
Volume	30
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4020(01)97103-0
State	Published - 1974
Externally published	Yes

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AB - Some reactions of benzobarbaralone 3 have been studied. Ring expansion occurs in reaction of 3 with diazomethane-lithium chloride to yield benzobullvalone 5 and the spirooxirane 6. The tosylhydrazone of 5 was converted to the fluxional benzobullvalene 9. Decarbonylation of 3 to benzocyclooactatetraene occurs upon irradiation. On reaction with Fe2CO)9, 3 gives a σ-π allyl tricarbonyliron complex, 11, with rearranged skeleton.

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Some chemistry of 6,7-benzotricyclo[3.3.1.0^2,8]-nona-3,6-dien-9-one (benzobarbaralone)

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