Wittig-type reactions of 2-lithio-2-trimethylsilyl-1,3-dithian and related reactions
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2272-2277
- https://doi.org/10.1039/p19730002272
Abstract
2-Lithio-2-trimethylsilyl-1,3-dithian reacts with carbonyl compounds, R1R2CO, to give alkylidenedithians, [graphic omitted]CR1R2(after acidic hydrolysis), potentially valuable synthetic intermediates for C1 homologation (e.g.→ R1R2CH·CHO or R1R2CH·CO2H). In similar reactions, acetyl chloride appears to yield [graphic omitted](SiMe3)·C(:CH2)·OAc, styrene oxide gives [graphic omitted](SiMe3)·CH2·CH(OH)Ph, and cis-[PtCl2(PPh3)2] gives cis-[PtCl{[graphic omitted]}(PPh3)2]. A homologous lithium reagent [graphic omitted]Li·CH2·SiMe3 with benzaldehyde furnishes [graphic omitted](CH2·SiMe3)·CH(OH)Ph.Keywords
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