40. The Influence of the Nitro-group upon Side-chain Reactivity. Part II. The Inhibition of the Influence of the Nitro-group Upon Α-proton- Extraction from 4-nitrobenzyl Chloride

Author

• Samir B. Hanna, Missouri University of Science and Technology
• Youssef Iskander
• Adib Salama

Abstract

The rates of liberation of chloride ion from 3-hydroxy- and 3-methoxy-4-nitrobenzyl chloride have been measured in initially neutral and in alkaline aqueous acetone and aqueous dioxan. In alkaline media, the formation of derivatives of 4,4′-dinitrostilbene was inhibited by the presence of the O-substituent ortho to the nitro-group, and the rate of reaction was similar to that of the alkaline hydrolysis of benzyl chloride. An o-methoxyl group was less effective. It is suggested that the electron-withdrawing power of the nitro-group is reduced by mesomeric interaction with adjacent OMe and especially O^- substituents.

Recommended Citation

S. B. Hanna et al., "40. The Influence of the Nitro-group upon Side-chain Reactivity. Part II. The Inhibition of the Influence of the Nitro-group Upon Α-proton- Extraction from 4-nitrobenzyl Chloride," Journal of the Chemical Society Resumed, pp. 221 - 222, Royal Society of Chemistry, Jan 1961.

The definitive version is available at https://doi.org/10.1039/JR9610000221

Department(s)

Chemistry

International Standard Serial Number (ISSN)

0368-1769

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2026 Royal Society of Chemistry, All rights reserved.

Publication Date

01 Jan 1961