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Bromination of 2,3-Dihydro-6-(hydroxyphenyl)-1,4-diazepinium Salts

✍ Scribed by Lloyd, Douglas ;Reichardt, Christian ;Struthers, Margot

Publisher: John Wiley and Sons
Year: 1986
Tongue: English
Weight: 367 KB
Volume: 1986
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198619860808

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✦ Synopsis

2,3-Dihydro-6-(4-hydroxyphenyl)-l,4-diazepinium salts 3a, b are readily mono-(+ 4a, b) and di-brominated (+ 5a, b) at the rneta-postion of the phenyl substituent. 2,3-Dihydro-6-(3hydroxyphenyl)-l,4-diazepinium salts 6a, b are readily mono-brominated (+ 7a, b) at the para-position of the phenyl substituent. A second bromination (-+ Sa, b) takes place at an ortho-position, surprisingly, since ortho-positions of 6-aryl substituents in 1,4-diazepinium salts are usually not susceptible to electrophilic attack. Mechanistic features of these brominations are considered. -1,2-Dihydro-5-(hydroxyphenyl)-2-oxopyrimidinium salts 11 a, b

were not brominated under similar conditions.

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