SMALL-RING COMPOUNDS. XXVIII. ISOTOPE-POSITION REARRANGEMENTS OF ALLYLCARBINYL GRIGNARD REAGENTS1

MS Silver, PR Shafer, JE Nordlander…

Index: Silver,M.S. et al. Journal of the American Chemical Society, 1960 , vol. 82, p. 2646 - 2647

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Citation Number: 61

Abstract

The typical orange color of a solution of racemic methylethylphenylbenzylidenephosphorane (I) in ether is not discharged when 1.45 equivalents of benzonitrile is added and the mixture stirred at 25'for 12 hours. However, removal of the ether and treatment of the residue with a solution of potassium hydroxide in aqueous methanol under reflux gives desoxybenzoin (11) in 78y0 yield and racemic ...