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• W2321869587 abstract "Photoinduced reactions of bicyclopropylidene (BCP) with para-quinones (p-quinones) including benzoquinones, naphthoquinones, and anthraquinones were found to proceed via different cycloaddition pathways and lead to diverse polycyclic products bearing spiropropyl moiety. Photocycloaddition of BCP with benzoquinones gave spirooxetanes as the primary products, which upon irradiation were able to rearrange into the spiro[4.5]deca-6,9-diene-2,8-diones as secondary photoproducts. Chemoselectivity of the photocycloaddition of BCP with naphthoquinones relies largely on the substitution groups linked to the C═C in between the two carbonyl groups to give different types of products. Photoreaction of BCP with 9,10-anthraquinone gave not only the spirooxetane product, but also a novel spiro[indan-1,1′-phthalan]-3′-one product whose formation might be initiated by a transannular attack of the C4 cyclopropyl radical to the para-carbonyl group. Mechanisms involved in the formation of diverse primary or secondary products in the photoreactions of BCP with p-quinones were proposed. Some of the photoreactions also hold potentials as useful synthetic protocols for important spiropolycyclic compounds such as sesquiterpenes." @default.
• W2321869587 created "2016-06-24" @default.
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• W2321869587 creator A5073216396 @default.
• W2321869587 creator A5086664284 @default.
• W2321869587 date "2013-06-03" @default.
• W2321869587 modified "2023-10-17" @default.
• W2321869587 title "Photoinduced Reactions of <i>para</i>-Quinones with Bicyclopropylidene Leading to Diverse Polycyclic Compounds with Spirocyclopropanes" @default.
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• W2321869587 doi "https://doi.org/10.1021/jo4008767" @default.
• W2321869587 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23692405" @default.
• W2321869587 hasPublicationYear "2013" @default.
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