Hindered organoboron groups in organic synthesis. 13. The direct production of ketones from aliphatic aldehydes by a unique variant of the boron-wittig reaction

A Pelter, K Smith, S Elgendy, M Rowlands

Index: Pelter, Andrew; Smith, Keith; Elgendy, Said; Rowlands, Martin Tetrahedron Letters, 1989 , vol. 30, # 41 p. 5643 - 5646

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Citation Number: 25

Abstract

Abstract In the presence of trifluoroacetic anhydride or N-chlorosuccinimide, aliphatic aldehydes react with dimesitylboron stabilised carbanions to give, after work up, the corresponding ketones, a process which is unique among Wittig type reactions. Yields of ketones are satisfactory in all cases except those involving the anion derived from the parent compound dimesitylmethylborane, which gives the corresponding alkenes.