Green, Ivan R.October, Natasha2023-02-132023-02-132010Green, 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.5550190.0011.2061551-7004https://doi.org/10.3998/ark.5550190.0011.206http://hdl.handle.net/10566/8424The 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.17enChemistryOxygen heterocyclesLow temperature studiesNaphthopyranquinonesArticle