Meyers' research groups have investigated many aspects of reaction mechanisms, single-electron-transfer (SET) reactions, carbanion reactivity, organosulfur chemistry, doisynolic-acid estrogens, phase-transfer deprotonations-D/H exchange, stereo-chemical consequences of reactions at the 9-position of rotationally hindered 9-substituted fluorenes, chirality at N-1 and N-2 of urazole and related moieties in crystalline derivatives and the diastereospecific formation of their nucleosides, such as the D- and L-2-deoxyribosides.
His group has resolved estrogenic doisynolic acids (the methyl ethers and free phenols) into their (+) and (-) enantiomers, and with the collaboration of physiologists at this University and endocrinologists at Washington University School of Mediciine is studying the mechanism of their estrogenic activity in vivo in female and male rats and in vitro. A study of the anti-breast cancer activity of the two enantiomers compared with Tamoxifen (hydroxytamoxifen) as the standard, is being undertaken.
The study of rotationally restricted sterically hindered 9-substituted fluorenes has led to the discovery of unprecedented reactions and pathways. An example is the surprising specific monochlorination with SOCl2 of one methyl group of sp-9-(o-t-butylphenyl)-9-fluorenol (sp- I) with concurrent replacement of the 9-OH by an H transferred from the methyl group (sp- II). Occurring via the 9-cation, this reaction apparently involves an intramolecular SN2 in which Cl- attacks a methyl from which an H- "leaving group" is displaced onto the 9-cation, the stereochemical result being configurational retention. In contrast, when the same substrate is treated with CH3SH, H+, the 9-cation itself is attacked by the reagent from the least hindered side leading to the formation of the ap-9-SCH3 (ap- II) derivative in a clean inversion of configuration. X-Ray crystallography attests to the absolute identification of thesestructures, shown in the below Figure.
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