✍ Scribed by Alain Krief; Jamal Bousbaa
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l-Methoxy-benzyllithiums bearing suitably positioned C,C double bonds possess a high propensityto producea five or a six memberedcycle by carbocyclisationreaction.The reaction proceeds completely stereoselectively and produces a five membered cycle possessingthe cis-stereochemistry between the methoxy and the adjacent methyl group. @ 1997publishedby F,lsevier science Ltd.
We have already described that benzyllithiums with built-in C,C double bonds 2, readily available from the corresponding methylseleno derivatives 1possessa high propensityto cycliseto cyclopentyl methyllithiums.We also found that the structure and the stereochemistryof the compounds(3-5) produced after methanolysis,depends upon
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Although I-methoxy-l -methylseleno-toluene is efficiently metallated by KDA, the same compound as well as its higher homologies react with t-butyllithium producing 1-methoxy benzyllithiumsvia the C-Se bond cleavage.These speciesare efficientlyalkylatedby alkyl halides, even the secondary ones and re
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