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Diels-Alder cycloadditions: 3-(p-toluenesulfonyl)-2-propenal as dienophile

✍ Scribed by Abdelkhalek Riahi; Jacques Muzart; Jean-Pierre Pete

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 279 KB
Volume: 111
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19921110702

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✦ Synopsis

Abstract

The cycloadditions of 3‐(p‐toluenesulfonyl)‐2‐propenal with cyclopentadiene, 1,3‐cyclo‐hexadiene, 1‐methoxy‐1,3‐cyclohexadiene, 1‐(trimethylsilyloxy)‐1,3‐butadiene, or 1,3‐diphenyliso‐benzofuran have been easily carried out at room temperature in the absence of catalyst. In contrast, furan has led to a Michael‐type addition. The basic elimination of the sulfonyl moiety of a cyclo‐adduct has shown that this dienophile is a synthetic equivalent of propynal.

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