✍ Scribed by Alain Krief; Jamal Bousbaa
No coin nor oath required. For personal study only.
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 react with THF in the presence of BF3-0Et2 to produce the homologated tatrahydropyranderivative in good yield. 01997 Published by Elsevier Science Ltd.
a-Methoxyalkyl selenides proved to be useful compounds in synthesis allowing, by cleavage of their C-Se bond,
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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 metho
nBuLi solution (5 mmol: in hexanej added. On warming to room temperature the original yellow solution changed color from green to reddish-brown. and gdS evolution was observed. After the mixture had been stirred at room temperature for 30 min the resulting clear yellow solution was refrigerated over