Pentatomic heteroaromatic cations. Part VI. New syntheses of aldehydes and ketones by reaction of 1,3-benzodithiolylium salts with Grignard reagents
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 17,p. 1886-1889
- https://doi.org/10.1039/p19760001886
Abstract
2-Substituted and 2,2-disubstituted 1,3-benzodithioles are formed when 1,3-benzodithiolylium and 2-phenyl-1,3-benzodithiolylium perchlorates, respectively, react with Grignard reagents. The products can be hydrolysed to aldehydes and ketones by treatment with chloramine τ followed by mercury(II) chloride. This procedure offers a sound alternative method for the synthesis of aldehydes by formylation of Grignard reagents, and it suggests a new route for the total synthesis of symmetric and asymmetric ketones from alkyl and aryl halides via such reagents.Keywords
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