Title: Preparation and some reactions of neophyltin anions
Abstract: A study on the preparation of trineophyltin and mixed methylneophyltin anions and subsequent reactions of these anions is reported. It was found that whereas mixed hydrides MenNph3−nSnH (n = 1,2) react with NaH in DMSO to give the corresponding organotin sodium anions (60–70% yield), trineophyltin hydride reacts with NaH to give hexaneophylditin as the only product (32%). The reaction of tin halides MenNph3−nX (X = Cl, Br; n = 0, 1, 2) with lithium in THF yields the corresponding organotinlithium anions (70%). The tin anions were reacted with various alkyl halides. The 1,4 addition of trineophyltinlithium (10∗) to α,β-unsaturated enones followed by the reaction of the intermediate carbanions with methyl iodide, leads with benzylideneacetone to a mixture of the corresponding threo (34%) and erythro (25%) diastereoisomers. Under the same reaction conditions, the addition of 10∗ to chalcone proceeded with complete stereoselectivity to give the diastereoisomer threo (60%) as the only product. Full 1H and 13C NMR data of the new organotins are given.
Publication Year: 1995
Publication Date: 1995-05-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 11
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