Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 13
239
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Three-Component Reactions of Ketene Dithioacetals, Aldehydes, and Arenesulfinic Acids: Facile Synthesis of Allylic Sulfones

, , , , , & show all
Pages 1930-1937 | Received 01 Nov 2013, Published online: 29 May 2014
 

Abstract

A facile and efficient synthesis of allylic sulfones via sulfuric acid–mediated three-component reactions of easily available ketene dithioacetals, aldehydes, and arenesulfinic acids is presented. The reaction features low cost and good yields.

GRAPHICAL ABSTRACT

Notes

a Reaction conditions: 1a (1.0 mmol), 2a (2.0 mmol), 3a (3.0 mmol), solvent (5.0 mL), room temperature.

b Isolated yields.

c Stirring at 35 °C.

d 1.2 equiv of 2a was used, and by-product A was isolated in 8% yield.

e 2.0 equiv of 3a was used, and by-product A was isolated in 12% yield.

f With recovery of 26% of 1a.

g No reaction.

h With recovery of 67% of 1a.

a Reaction conditions: 1 (1.0 mmol), 2 (2.0 mmol), 3 (3.0 mmol), H2SO4 (0.5 mmol), MeCN (5.0 mL), room temperature.

b Isolated yields.

c By-product A was isolated in 19% yield.

d Stirring at reflux temperature.

e 3.0 equiv of paraformaldehyde was used.

f TiCl4 (1.5 mmol) used as promoter and CH2Cl2 as solvent.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.