Role of the methoxy group in product formation via TiCl4 promoted 4-phenyldioxolane isomerizations

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dc.contributor.authorGreen, Ivan R.
dc.contributor.authorOctober, Natasha
dc.date.accessioned2023-02-13T11:21:48Z
dc.date.available2023-02-13T11:21:48Z
dc.date.issued2010
dc.description.abstractThe product distribution obtained from the TiCl4 initiated intramolecular isomerizations of 4- methoxyphenyl- and trimethoxyphenyldioxolanes at -78 oC, -30 oC and 0 oC provided insights into the important regiochemical role played by these groups in such Mukaiyama- type rearrangements through their resonance effects on the aryl ring of the dioxolanes.Our interest in naphthopyranquinones as potential antimicrobial and antibiotic agents has extended over two decades1-6 as a result of their well documented importance.7,8 Additionally, the synthesis of benzopyrans as model systems has received attention by ourselves6,9-13 and others.14- 16 Of particular interest to us was our earlier discovery of a TiCl4 - induced intramolecular isomerization in which phenyl- and naphthyldioxolanes were stereoselectively transformed into their corresponding benzo- and naphthopyrans.17en_US
dc.identifier.citationGreen, I. R., & October, N. (2010). Role of the methoxy group in product formation via TiCl4 promoted 4-phenyldioxolane isomerizations. ARKIVOC, 71-96. https://doi.org/10.3998/ark.5550190.0011.206en_US
dc.identifier.issn1551-7004
dc.identifier.urihttps://doi.org/10.3998/ark.5550190.0011.206
dc.identifier.urihttp://hdl.handle.net/10566/8424
dc.language.isoenen_US
dc.publisherARKAT USA INCen_US
dc.subjectChemistryen_US
dc.subjectOxygen heterocyclesen_US
dc.subjectLow temperature studiesen_US
dc.subjectNaphthopyranquinonesen_US
dc.titleRole of the methoxy group in product formation via TiCl4 promoted 4-phenyldioxolane isomerizationsen_US
dc.typeArticleen_US

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