Boblitt, Robert L.2022-06-202022-06-20197413805680https://hdl.handle.net/10657/9514To study the relationship between side-chain methylation and selective beta-receptor antagonism, eight aminophenoxybutanols were prepared, comprised of two series containing four compounds each: (A) 3-amino-1-phenoxybutan-2-ols(I), and (B) l-amino-3-phenoxybutan-2-ols(II). Synthesis was achieved by treating two isomeric phenols (4,4-dimethylphenol or 4-ethylphenol) with 3-bromo-1,2-epoxybutane, catalyzed with BF[subscript 3]-etherate, which resulted in a mixture of 3-bromo-1-phenoxy- and 1-bromo-3-phenoxybutan-2-ols. Subsequent refluxing with i-propyl- or t-butylamine afforded I and II. The mixture thus formed was separated by column chromatography and found to consist of approximately 30% I and 70% II. The structure of II was unexpected; it was assumed that a 3-amino-2-phenoxybutan-l-ol (the "abnormal" product) would prevail. PMR, CMR and mass spectral data were employed for structure elucidation.application/pdfenThis item is protected by copyright but is made available here under a claim of fair use (17 U.S.C. Section 107) for non-profit research and educational purposes. Users of this work assume the responsibility for determining copyright status prior to reusing, publishing, or reproducing this item for purposes other than what is allowed by fair use or other copyright exemptions. Any reuse of this item in excess of fair use or other copyright exemptions requires express permission of the copyright holder.Thesisreformatted digital