A new synthesis of trans-2,3-diaryloxiranes and 2-(1 H -benzo[ d ][1,2,3]-triazol-1-yl)-1-arylethanols via the reactions of 1-benzyl-3- methylbenzo-triazolium ylide with aryl aldehydes
1-Benzyl-3-methylbenzotriazolium ylide was formed by the reaction of 1-benzyl-3-methylbenzotriazolium iodide with t-BuOK. Subsequently it reacted with various aryl aldehydes to give the corresponding trans-2,3-diaryloxiranes and 2-(1H-benzo-[d][1,2,3]triazol-1-yl)-1-arylethanols in moderate to high yields. Georg Thieme Verlag Stuttgart · New York.
Metalation of o-Halostyrene Oxides. Preparation of Benzocyclobutenols
o-Bromo- and o-iodostyrene oxides are converted in fair to good yield to benzocyclobutenols upon treatment with n-BuLi and MgBr2 in THF or ether at -78 deg C, followed by warming to room temperature.The reaction involves initial halogen-lithium exchange followed either by MgBr2-initiated opening of the epoxide function to a haloalkoxide or rearrangement of the epoxide function to a ketone or aldehyde followed by cyclization.Benzocyclobutenol formation was not successful in the case of o-halostilbene oxides.
Akguen, Eyup,Glinski, Margaret B.,Dhawan, Kasturi L.,Durst, Tony
p. 2730 - 2734
(2007/10/02)
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