Issue 15, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The Diels–Alder reactivity of (E)-3-phenylsulfonylprop-2-enenitrile, a cyanoacetylene equivalent

Pamela J. Bradleya  and  David H. Grayson*a  

* Corresponding authors

a University Chemical Laboratory, Trinity College, Dublin 2, Ireland

Abstract

(E)-3-Phenylsulfonylprop-2-enenitrile undergoes facile Diels–Alder reactions, moderate regioselectivity being observed with several unsymmetrical dienes. Danishefsky's diene and furfuryl alcohol react regioselectively. The cycloadducts formed with cyclopentadiene and with anthracene undergo base-catalysed elimination of benzenesulfinic acid to yield α,β-unsaturated nitriles.

Graphical abstract: The Diels–Alder reactivity of (E)-3-phenylsulfonylprop-2-enenitrile, a cyanoacetylene equivalent

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B203391G
Article type
Paper
Submitted
05 Apr 2002
Accepted
19 Jun 2002
First published
08 Jul 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1794-1799

Permissions

Request permissions

The Diels–Alder reactivity of (E)-3-phenylsulfonylprop-2-enenitrile, a cyanoacetylene equivalent

P. J. Bradley and D. H. Grayson, J. Chem. Soc., Perkin Trans. 1, 2002, 1794 DOI: 10.1039/B203391G

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