Lithium keten thioacetalides. Factors influencing α-versusγ-alkylation
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2678-2682
- https://doi.org/10.1039/p19800002678
Abstract
Alkylation of the lithium salt of the vinyl-1,3-dithian (2; R = CH3) occurred exclusively at the α-carbon. However both α- and γ-alkylation was observed with the substrate (2; R = C6H5). A systematic investigation revealed that the α : γ ratio is correlated with the hardness of both the leaving group and the alkyl group of the alkylating agent. An occasionally formed side-product from the reactions of (2; R = C6H5) was the α,γ-dimer (11) of the anion (6; R = C6H5).Keywords
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