Add time:08/17/2019         Source:sciencedirect.com

The readily available 2,3-dibromo-1-(phenylsulfonyl)-1-propene (DBP) undergoes facile reaction with several 1,3-dicarbonyl compounds under basic conditions to give (phenylsulfonyl)methyl substituted cyclopentenones. The pendant sulfonyl group at the C3 position of the cyclopentenone ring offers a versatile site for further elaboration via alkylation. These cyclic α-enone systems are easily metallated with sodium hydride, and the resultant carbanion undergoes both bimolecular and intramolecular alkylations. The overall sequence provides a simple and efficient route to functionalized cyclopentenones. The alkylated sulfones were easily desulfonylated upon heating with tri n-butyltin hydride and AIBN in toluene at 110 °C. A novel base-induced transformation was observed using 3-(phenylsulfonyl)methyl-2-(4-iodobutyl)cyclopentenone. Treatment of this compound with one equivalent of NaH in the presence of HMPA afforded 4-methylene-spiro[4.4]non-2-en-1-one. This reaction proceeds by initial γ-alkylation followed by a 1,3-hydrogen shift and subsequent 1,4-elimination of sulfinate anion.

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