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Synthesis of 1‐nitro‐2‐( p ‐hydroxyphenyl)[2‐ 3 H 1 ]ethane
Author(s) -
Halkier Barbara Ann,
Olsen Carl Erik,
Marcussen Jan
Publication year - 1991
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580290102
Subject(s) - chemistry , nitro , nitromethane , olefin fiber , sodium hydride , selective reduction , medicinal chemistry , hydride , organic chemistry , stereochemistry , hydrogen , alkyl , catalysis , polymer
A racemic mixture of ( R )‐ and ( S )‐1‐nitro‐2‐( p ‐hydroxyphenyl)[2‐ 3 H 1 ]ethane was synthesized from 1‐nitro‐2‐( p ‐hydroxyphenyl)ethene by selective reduction of the olefin with sodium boro[ 3 H]hydride. The nitroethene was obtained in one step by condensation of p ‐hydroxybenzaldehyde with nitromethane. The produced racemic mixture is to be used in studies regarding the involvement of 1‐nitro‐2‐( p ‐hydroxyphenyl)ethane as intermediate in the biosynthesis of tyrosine‐derived cyanogenic glucosides and glucosinolates.