ChemInform Abstract: Cycloaddition Reactions of 1-Phenylseleno-2-(p-toluenesulfonyl)ethyne

Autor: Masood Parvez, Jerry A. Taylor, Thomas G. Back, Richard J. Bethell, Daniel Wehrli
Rok vydání: 2010
Předmět:
Zdroj: ChemInform. 31
ISSN: 1522-2667
0931-7597
DOI: 10.1002/chin.200008047
Popis: 1-Phenylseleno-2-(p-toluenesulfonyl)ethyne (1) is an effective dienophile and dipolarophile. It underwent facile Diels−Alder reactions with a variety of dienes to afford vicinal sulfone- and selenide-functionalized 1,4-cyclohexadienes. Unexpected regiochemistry that is the opposite of what is obtained with simple acetylenic sulfones was observed with several unsymmetrical dienes containing methyl or methoxy substituents at the 1- or 2-position. Acetylene 1 reacted with (trimethylsilyl)methyl azide, diazomethane, and 2,4,6-trimethylbenzonitrile N-oxide via 1,3-dipolar cycloadditions to afford the corresponding triazole, 1,2-diazole, and isoxazole products. It also underwent an ene reaction with β-pinene that showed anomalous regiochemistry compared to other acetylenic sulfones. The Diels−Alder cycloadducts obtained from the reaction of 1 with 2,3-dimethyl-1,3-butadiene and 1,3-cyclohexadiene were readily converted into the corresponding β-keto sulfones and ketones, thus rendering 1 as the synthetic equival...
Databáze: OpenAIRE
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