Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Mass Spectral Rearrangement : A Scope of Rearrangement of Alkylaminomethyl Group to the Ring in 1-Alkylamino-3-aryloxy-2-propanol Derivatives
SEIJIRO HONMAYOSHIHIRO KAWABEAKIRA KAMBEGAWA
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Keywords: propranolol
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1977 Volume 25 Issue 8 Pages 1843-1850

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Abstract
The mass spectra of 1-alkylamino-3-aryloxy-2-propanol exhibited prominent losses of the elements of acetaldehyde from the molecular ion. The ion showed an unexpected rearrangement of alkylamino group from 1-alkylaminopropane to aryl group with the formation of six-membered transition state. The new McLafferty-type rearrangement in these compounds was not shown in the replacement of the element of nitrogen by sulfur and oxygen on alkylamino group and also in addition of methylene group to alkylamino group to form alkylaminobutane. The mechanism of the rearrangement was discussed in detail.
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© The Pharmaceutical Society of Japan
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