Conclusions
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1.
Primary and secondary alkyl bromides and iodides react with the silver salts of N-nitroarenesulfonamides to form usually a mixture of N-and O-alkylation products. Tertiary alkyl iodides, according to the structure of the alkyl group, afford either the nitroamides or O-alkylation products.
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2.
The contribution of O-alkylation increases on passing from primary to secondary alkyl halides and from iodides to bromides, and decreases when electron-acceptor groups are introduced into the aromatic ring of the N-nitroarenesulfonamide.
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3.
The contribution of O-alkylation increases on passing from protic polar or aprotic dipolar to nonpolar solvents.
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Literature cited
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 659–662, March, 1976.
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Luk'yanov, O.A., Shlykova, N.I. & Tartakovskii, V.A. Alkylation of salts of N-nitroarenesulfonamides by alkyl halides. Russ Chem Bull 25, 644–646 (1976). https://doi.org/10.1007/BF01106672
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DOI: https://doi.org/10.1007/BF01106672