ORGLIST: Ylide

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From: Bhushan Deodhar (bsdeodhar$##$gmail.com)
Date: Fri Nov 21 2008 - 14:57:23 EST


Dear Colleagues,
                       I am trying to convert ethyltriphenyl phosphonium
bromide [ wittig salt] into Ethylidenetriphenylphosphorane by use of a
strong base.I did many reactions using BuLi,Sodium Amide by conventioanl
methods listed in many journals.Now most of the journals say that the
solvent for BuLi and other typical reducing agents is THF,but i found that
the salt [ ethyltriphenyl phosphonium bromide] is not soluble in it,but i
still went ahead and did the reaction using THF as a suspension with the
salt in it.But i don't get any kind of conversion.Please also note that i am
taking typical precautions such as Argon atmosphere,Distilled solvents
etc..Is the ylide stable after formation?I am confused with the above,Any
replies and suggestions will be appreciated.

Thanks,
           Bhushan


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