Issue 9, 1975
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Nucleophilic attacks on carbon–carbon double bonds. Part XXIII. Substitution of β-chloro-α-phenylacrylonitriles

Zvi Rappoport  and  Alain Topol  

Abstract

Substitutions of (E)- and (Z)-β-chloro-α-phenylacrylonitriles by arenethiolate, azide, and ethoxide ions proceed with retention of configuration, while reactions with piperidine or morpholine give the same enamino-nitrile from the two isomeric chlorides. The second-order rate constants give the nucleophilicity order ArS– > EtO– > piperidine > PhO– > morpholine > N3–. These results are discussed in terms of the addition–elimination route of nucleophilic vinylic substitution, and the data are compared with those found for related reactions.

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/P29750000982
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1975, 982-988

Permissions

Request permissions

Nucleophilic attacks on carbon–carbon double bonds. Part XXIII. Substitution of β-chloro-α-phenylacrylonitriles

Z. Rappoport and A. Topol, J. Chem. Soc., Perkin Trans. 2, 1975, 982 DOI: 10.1039/P29750000982

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements