Unexpected Ritter Reaction During Acid‐Promoted 1, 3‐Dithiol‐2‐one Formation. Issue 5 (17th May 2013)

• Record Type: Journal Article
• Authors: Dumur, Frédéric; Mayer, Cédric R.
• Is Part Of: Helvetica chimica acta. Volume 96:Issue 5(2013:May)
• Page Start: 889
• Page End: 896
• Publication Date: 2013-05-17
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201200311
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A series of aryl‐substituted 1, 3‐dithiol‐2‐ones was prepared by the <italic>Bhattacharya</italic><italic>Hortmann</italic> cyclization method. Unexpectedly, a <italic>Ritter</italic> reaction occurred during the acid‐catalyzed cyclization at the cyano group of the aryl substituents and 1, 3‐dithiol‐2‐ones bearing a carboxy or a carboxamide group could be selectively obtained (see <bold>1</bold> and <bold>2a</bold> in <italic>Scheme 1</italic>). The formation of the acid or the amide functionality was temperature‐dependent so that the one or the other group could be introduced selectively by modifying the reaction temperature.</p> </abstract>