Substituent effects of phosphorus and arsenic containing groups in aromatic substitution. VI. Orientation in nitration of some anilides and phenyl esters
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The orientation in nitration of N-acyl derivatives of aniline and O-acyl derivatives of phenol in aqueous H2SO4 and in acetic anhydride has been studied. Acetyl and methanesulfonyl derivatives are exclusively ortho/para directing, whereas the N- and O-phosphorylated compounds yield in both media considerable amounts of the meta isomer. The observed differences in orientation are discussed in terms of different protonation sites and strong πp−πd interactions of the oxygen or nitrogen and the P(IV) atom.
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1956 ◽
Vol 21
(6)
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pp. 1500-1512
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1965 ◽
Vol 30
(4)
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pp. 940-951
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1969 ◽
Vol 34
(11)
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pp. 3325-3335
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1983 ◽
Vol 48
(2)
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pp. 586-595
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