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N-(1,1-disubstitutedpropargyl)anilines can be cyclised to 2,2-disubstituted-1,2-dihydroquinolines by refluxing them in toluene containing cuprous chloride. Electron donating groups in the para position of the ring enhance the reaction rate and electron withdrawing groups markedly decrease the rate. The derived N-acetyldihydroquinolines can be cis dichlorinated and selectively monodechlorinated at...
Hydroxyselenation of terminal or cyclic allylic alcohols occurs with high regio- and stereoselectivity to give β,β -dihydroxyphenylselenated adducts in high yields. A mechanism for this selectivity is proposed. The utility of these adducts is illustrated by the conversion of the hydroxyselenide (9a) to the epoxide (11) via the intermediacy of a selenone.
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